NPASS Compound

Natural Product: NPC233122

Natural Product ID	NPC233122
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MIJYXULNPSFWEK-IBSLXNBYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	7061300
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 81 85 0 0 0 0 0 0 0 0999 V2000 -4.7652 2.4883 0.7817 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9081 1.5361 -0.3851 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6565 2.2694 -1.4789 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7368 0.3487 0.0253 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9818 -0.6931 0.7564 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6339 -1.0367 0.1964 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9029 -1.9323 1.2059 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4689 -2.1431 0.8353 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6948 -0.8360 0.7026 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7089 -0.2055 2.0763 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4389 -0.0166 -0.2714 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9555 0.4653 -1.3736 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4550 0.2257 -1.7762 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2195 0.0767 -0.4491 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6768 0.2691 -0.6743 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2033 -0.4455 -1.8839 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8671 1.7688 -0.9662 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0006 2.3523 -0.1890 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2288 1.5098 -0.1307 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8979 0.2091 0.5303 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6966 -0.8972 -0.0791 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3668 0.3315 1.9911 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4330 -0.0025 0.5821 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0666 -1.3470 1.1956 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6121 -1.2529 1.5488 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7457 -1.0916 0.3114 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7844 -2.4032 -0.4218 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1821 2.2374 0.6198 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8720 0.2649 0.0459 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5621 1.1262 -0.9473 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8071 -1.7818 -1.0701 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3153 -1.4798 -2.1796 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5901 -2.9561 -1.1027 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7282 1.9548 1.7536 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7210 3.0825 0.8084 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9575 3.2159 0.6500 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7783 1.5381 -2.3208 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1106 3.1273 -1.8747 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7007 2.5164 -1.1591 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5299 0.7456 0.7181 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2996 -0.0296 -0.8607 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5890 -1.6449 0.7174 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8952 -0.4642 1.8410 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0719 -1.6040 2.2473 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4073 -2.9228 1.1152 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4712 -2.7177 -0.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0315 -2.7952 1.6168 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7598 -0.0596 2.4335 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2305 0.7696 2.1292 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2872 -0.9670 2.7844 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5744 1.0569 -2.0332 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9108 1.0643 -2.3110 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4666 -0.7246 -2.3511 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8797 0.9870 0.1386 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4440 -0.4990 -2.6882 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0480 0.1426 -2.3555 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5970 -1.4383 -1.7099 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9590 2.3539 -0.7147 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0591 1.9567 -2.0400 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7008 2.6868 0.8420 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2862 3.3120 -0.7091 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6777 1.4079 -1.1365 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2954 -1.9110 0.1175 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7175 -0.9047 0.4110 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9296 -0.7408 -1.1603 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5390 -0.7169 2.3486 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3491 0.8323 2.0502 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5928 0.7748 2.6291 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0366 0.7381 1.3313 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3283 -2.1962 0.5709 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6346 -1.4190 2.1463 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5097 -0.2836 2.1214 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3292 -2.1231 2.1587 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1606 -2.4511 -1.3134 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5032 -3.1912 0.3402 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8131 -2.7020 -0.7337 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7506 2.7944 0.0337 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9393 0.8207 1.0300 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7489 0.6956 -1.9406 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9888 2.0999 -1.0402 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1350 -3.1258 -1.9383 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 19 28 1 0 11 29 1 0 29 30 1 0 6 31 1 6 31 32 2 0 31 33 1 0 30 2 1 0 29 6 1 0 26 9 1 0 26 14 1 0 23 15 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 7 44 1 0 7 45 1 0 8 46 1 0 8 47 1 0 10 48 1 0 10 49 1 0 10 50 1 0 12 51 1 0 13 52 1 0 13 53 1 0 14 54 1 1 16 55 1 0 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 18 60 1 0 18 61 1 0 19 62 1 6 21 63 1 0 21 64 1 0 21 65 1 0 22 66 1 0 22 67 1 0 22 68 1 0 23 69 1 1 24 70 1 0 24 71 1 0 25 72 1 0 25 73 1 0 27 74 1 0 27 75 1 0 27 76 1 0 28 77 1 0 29 78 1 1 30 79 1 0 30 80 1 0 33 81 1 0 M END

Standard InCHIKey	MIJYXULNPSFWEK-IBSLXNBYSA-N
Standard InCHI	InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21+,22-,23-,27+,28-,29-,30+/m1/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@H]2C1)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.36	Volume:	505.751 ? Van der Waals volume.
Dense:	0.902	LogP:	4.0 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.48 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.792 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.409	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.589	Fsp³:	0.9
MCE-18:	105.368 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.861	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.499	Promiscuous compounds:	0.073

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.419	MDCK Permeability:	-5.059
Pgp-inhibitor:	0.015	Pgp-substrate:	0.002
PAMPA:	0.999 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.076	30% Bioavailability (F30%):	0.015
50% Bioavailability (F50%):	0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.107	MRP1:	0.955
Plasma Protein Binding (PPB):	93.254%	Volume Distribution (VD):	-0.289
Fu:	6.674% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.835	BCRP inhibitor:	0.022
BSEP inhibitor:	0.89

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.91	CYP2C19-substrate:	0.585
CYP2C9-inhibitor:	0.372	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.254	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.318	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.352
HLM stability:	0.942 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.244

Half-life (T1/2):

0.826

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.052
Human Hepatotoxicity (H-HT):	0.593	Drug-induced Liver Injury (DILI):	0.271
AMES Toxicity:	0.242	Rat Oral Acute Toxicity:	0.278
Maximum Recommended Daily Dose:	0.484	Skin Sensitization:	0.655
Carcinogencity:	0.875	Eye Corrosion:	0.022
Eye Irritation:	0.556	Respiratory Toxicity:	0.889
Drug-induced Neurotoxicity:	0.016	Ototoxicity:	0.66
Hematotoxicity:	0.318	Drug-induced Nephrotoxicity:	0.776
Genotoxicity:	0.24	RPMI-8226 Immunitoxicity:	0.036
A549 Cytotoxicity:	0.062	Hek293 Cytotoxicity:	0.107
BCF:	1.805 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.221 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.592 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.052 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[10661881]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11430011]
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	stems	n.a.	n.a.	PMID[12350169]
NPO15915	Edgeworthia gardneri	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387673]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[28294414]
NPO16125	Micromonas pusilla	Species	Mamiellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15349	Acacia sparsiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14936	Agave shawii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15205	Alaria crispa	Species	Alariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9479	Ambrosia grayi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13139	Anatheca montagnei	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11808	Ania latifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14807	Arenaria juncea	Species	Scolopacidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11436	Baeomyces roseus	Species	Baeomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5866	Bitis arietans	Species	Viperidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15697	Camellia sasanqua	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26426.1	Cassia javanica subsp. nodosa	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14463	Dirca occidentalis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15797	Drypetes littoralis	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15915	Edgeworthia gardneri	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13442	Eucalyptus regnans	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12293	Euphorbia iberica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24409	Evasterias troschelii	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5047	Evodiopanax innovans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO820	Grindelia perennis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11002	Hopea jucunda	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12490	Lecidea speirodes	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2038	Myrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14313	Pachybasium candidum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16718	Pinna nobilis	Species	Pinnidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16475	Plumbago pulchella	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2827	Plumeria alba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16557	Polygala ruwenzoriensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8804	Raputia simulans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20219	Rhizobium etli	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27733	Rosa hybrid cultivar	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16796	Rumex conglomeratus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4589	Sarcotragus spinosulus	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15588	Senecio desfontainei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11987	Silene inflata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11994	Thesium humile	Species	Thesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16025	Werneria decora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26426.1	Cassia javanica subsp. nodosa	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15697	Camellia sasanqua	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15915	Edgeworthia gardneri	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16125	Micromonas pusilla	Species	Mamiellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13139	Anatheca montagnei	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11994	Thesium humile	Species	Thesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14936	Agave shawii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4589	Sarcotragus spinosulus	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9479	Ambrosia grayi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15797	Drypetes littoralis	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11002	Hopea jucunda	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11987	Silene inflata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16718	Pinna nobilis	Species	Pinnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11436	Baeomyces roseus	Species	Baeomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16557	Polygala ruwenzoriensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16796	Rumex conglomeratus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15588	Senecio desfontainei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26426.1	Cassia javanica subsp. nodosa	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14463	Dirca occidentalis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5866	Bitis arietans	Species	Viperidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27733	Rosa hybrid cultivar	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14313	Pachybasium candidum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15205	Alaria crispa	Species	Alariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15303	Phyllosma capensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11808	Ania latifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24409	Evasterias troschelii	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14807	Arenaria juncea	Species	Scolopacidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8804	Raputia simulans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16025	Werneria decora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16475	Plumbago pulchella	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12490	Lecidea speirodes	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15697	Camellia sasanqua	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5047	Evodiopanax innovans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15349	Acacia sparsiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12293	Euphorbia iberica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13442	Eucalyptus regnans	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15412	Proustia ilicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2038	Myrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20219	Rhizobium etli	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO820	Grindelia perennis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2827	Plumeria alba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC233122 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	21862
0.1-0.2	23351
0.2-0.3	3427
0.3-0.4	736
0.4-0.5	240
0.5-0.6	105
0.6-0.7	59
0.7-0.8	0
0.8-0.85	2
0.85-0.9	6
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC480946
1.0	High Similarity	NPC130577
1.0	High Similarity	NPC142415
1.0	High Similarity	NPC102683
0.85	High Similarity	NPC270768
0.85	High Similarity	NPC59263
0.85	High Similarity	NPC182797
0.85	High Similarity	NPC210106
0.85	High Similarity	NPC52169
0.85	High Similarity	NPC488562
0.8333	Intermediate Similarity	NPC198664
0.8226	Intermediate Similarity	NPC298554
0.7656	Intermediate Similarity	NPC228784
0.7656	Intermediate Similarity	NPC324341
0.7656	Intermediate Similarity	NPC601810
0.7619	Intermediate Similarity	NPC64872
0.7619	Intermediate Similarity	NPC84319
0.7619	Intermediate Similarity	NPC25906
0.7619	Intermediate Similarity	NPC52021
0.7619	Intermediate Similarity	NPC599947
0.746	Intermediate Similarity	NPC187722
0.7353	Intermediate Similarity	NPC474727
0.7344	Intermediate Similarity	NPC282616
0.7344	Intermediate Similarity	NPC275809
0.7344	Intermediate Similarity	NPC51700
0.7344	Intermediate Similarity	NPC121798
0.7344	Intermediate Similarity	NPC88716
0.7344	Intermediate Similarity	NPC234346
0.7344	Intermediate Similarity	NPC68160
0.7344	Intermediate Similarity	NPC606443
0.7231	Intermediate Similarity	NPC158141
0.7121	Intermediate Similarity	NPC202728
0.7121	Intermediate Similarity	NPC158059
0.7121	Intermediate Similarity	NPC293564
0.7097	Intermediate Similarity	NPC604575
0.7015	Intermediate Similarity	NPC91010
0.697	Remote Similarity	NPC231063
0.697	Remote Similarity	NPC282395
0.697	Remote Similarity	NPC130278
0.697	Remote Similarity	NPC110308
0.6866	Remote Similarity	NPC29765
0.6716	Remote Similarity	NPC106112
0.6716	Remote Similarity	NPC261935
0.6716	Remote Similarity	NPC481360
0.6712	Remote Similarity	NPC603645
0.6667	Remote Similarity	NPC130520
0.6618	Remote Similarity	NPC200752
0.6618	Remote Similarity	NPC120840
0.6567	Remote Similarity	NPC37038
0.6567	Remote Similarity	NPC171203
0.6567	Remote Similarity	NPC307426
0.6567	Remote Similarity	NPC98442
0.6567	Remote Similarity	NPC242468
0.6567	Remote Similarity	NPC112866
0.6522	Remote Similarity	NPC474963
0.6515	Remote Similarity	NPC477872
0.6471	Remote Similarity	NPC472149
0.6447	Remote Similarity	NPC204407
0.6418	Remote Similarity	NPC274330
0.6364	Remote Similarity	NPC280654
0.6364	Remote Similarity	NPC283849
0.6364	Remote Similarity	NPC28198
0.6364	Remote Similarity	NPC476123
0.6364	Remote Similarity	NPC606107
0.6338	Remote Similarity	NPC222047
0.6324	Remote Similarity	NPC7260
0.6324	Remote Similarity	NPC210037
0.6324	Remote Similarity	NPC229281
0.6324	Remote Similarity	NPC120968
0.6324	Remote Similarity	NPC156981
0.6324	Remote Similarity	NPC227467
0.6324	Remote Similarity	NPC273621
0.6265	Remote Similarity	NPC198621
0.6265	Remote Similarity	NPC216940
0.625	Remote Similarity	NPC96580
0.6232	Remote Similarity	NPC61543
0.6232	Remote Similarity	NPC293048
0.6232	Remote Similarity	NPC225585
0.6203	Remote Similarity	NPC286347
0.6173	Remote Similarity	NPC18982
0.6143	Remote Similarity	NPC136697
0.6125	Remote Similarity	NPC100383
0.6119	Remote Similarity	NPC161751
0.6119	Remote Similarity	NPC474972
0.6119	Remote Similarity	NPC600543
0.6111	Remote Similarity	NPC296164
0.6098	Remote Similarity	NPC475627
0.6087	Remote Similarity	NPC307282
0.6056	Remote Similarity	NPC191412
0.6056	Remote Similarity	NPC114159
0.6056	Remote Similarity	NPC6818
0.6032	Remote Similarity	NPC290598
0.6032	Remote Similarity	NPC30590
0.6	Remote Similarity	NPC101475
0.6	Remote Similarity	NPC609452
0.5976	Remote Similarity	NPC294112
0.5976	Remote Similarity	NPC284807
0.5972	Remote Similarity	NPC127689
0.5952	Remote Similarity	NPC488215
0.5942	Remote Similarity	NPC610937
0.5915	Remote Similarity	NPC139570
0.5915	Remote Similarity	NPC291028
0.5909	Remote Similarity	NPC235341
0.5904	Remote Similarity	NPC191410
0.589	Remote Similarity	NPC187933
0.589	Remote Similarity	NPC116457
0.5882	Remote Similarity	NPC262970
0.5857	Remote Similarity	NPC290972
0.5857	Remote Similarity	NPC306541
0.5857	Remote Similarity	NPC195019
0.5833	Remote Similarity	NPC263393
0.5833	Remote Similarity	NPC475472
0.5783	Remote Similarity	NPC473538
0.5775	Remote Similarity	NPC18872
0.5775	Remote Similarity	NPC290614
0.5775	Remote Similarity	NPC88116
0.5765	Remote Similarity	NPC270667
0.5765	Remote Similarity	NPC164194
0.5735	Remote Similarity	NPC72638
0.5714	Remote Similarity	NPC474806
0.5714	Remote Similarity	NPC133579
0.5672	Remote Similarity	NPC253807
0.5672	Remote Similarity	NPC158662
0.5652	Remote Similarity	NPC246708
0.5634	Remote Similarity	NPC32118
0.5632	Remote Similarity	NPC136877
0.5632	Remote Similarity	NPC12288
0.5618	Remote Similarity	NPC475311
0.5616	Remote Similarity	NPC118519
0.5616	Remote Similarity	NPC201657
0.5584	Remote Similarity	NPC188833
0.5584	Remote Similarity	NPC481362
0.5568	Remote Similarity	NPC174679
0.5568	Remote Similarity	NPC25605
0.5568	Remote Similarity	NPC279554
0.5568	Remote Similarity	NPC132126
0.5568	Remote Similarity	NPC56713
0.5568	Remote Similarity	NPC59804
0.5556	Remote Similarity	NPC271614
0.5556	Remote Similarity	NPC71074
0.5556	Remote Similarity	NPC37221
0.5556	Remote Similarity	NPC605937
0.5538	Remote Similarity	NPC27765
0.5538	Remote Similarity	NPC122418
0.5538	Remote Similarity	NPC491014
0.5522	Remote Similarity	NPC311078
0.5522	Remote Similarity	NPC34177
0.5506	Remote Similarity	NPC114441
0.5506	Remote Similarity	NPC127056
0.5506	Remote Similarity	NPC109079
0.5479	Remote Similarity	NPC259733
0.5479	Remote Similarity	NPC158371
0.5479	Remote Similarity	NPC207922
0.5479	Remote Similarity	NPC145667
0.5467	Remote Similarity	NPC324063
0.5465	Remote Similarity	NPC171007
0.5465	Remote Similarity	NPC190849
0.5465	Remote Similarity	NPC475611
0.5455	Remote Similarity	NPC601365
0.5444	Remote Similarity	NPC472949
0.5444	Remote Similarity	NPC6377
0.5444	Remote Similarity	NPC488561
0.5444	Remote Similarity	NPC208381
0.5435	Remote Similarity	NPC206232
0.5435	Remote Similarity	NPC14515
0.5405	Remote Similarity	NPC610635
0.5402	Remote Similarity	NPC22676
0.5385	Remote Similarity	NPC22956
0.5352	Remote Similarity	NPC17733
0.5352	Remote Similarity	NPC470629
0.5342	Remote Similarity	NPC38754
0.5342	Remote Similarity	NPC481314
0.5333	Remote Similarity	NPC25299
0.5333	Remote Similarity	NPC481322
0.5333	Remote Similarity	NPC481316
0.5326	Remote Similarity	NPC469945
0.5303	Remote Similarity	NPC120098
0.5294	Remote Similarity	NPC43353
0.5294	Remote Similarity	NPC196753
0.5286	Remote Similarity	NPC480950
0.5281	Remote Similarity	NPC605663
0.5278	Remote Similarity	NPC18064
0.5278	Remote Similarity	NPC2539
0.527	Remote Similarity	NPC173089
0.527	Remote Similarity	NPC87095
0.5269	Remote Similarity	NPC114304
0.5263	Remote Similarity	NPC157113
0.5217	Remote Similarity	NPC472608
0.5217	Remote Similarity	NPC40394
0.5217	Remote Similarity	NPC480924
0.5213	Remote Similarity	NPC104400
0.5213	Remote Similarity	NPC10320
0.5213	Remote Similarity	NPC180550
0.5213	Remote Similarity	NPC35405
0.5205	Remote Similarity	NPC301244
0.5205	Remote Similarity	NPC488519
0.52	Remote Similarity	NPC132824
0.52	Remote Similarity	NPC476992
0.5195	Remote Similarity	NPC481315
0.519	Remote Similarity	NPC54909

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC233122 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6408
0.1-0.2	2680
0.2-0.3	53
0.3-0.4	5
0.4-0.5	3
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.507	Remote Similarity	NPD7520	Phase 1

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data