NPASS Compound

Natural Product: NPC225779

Natural Product ID	NPC225779
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VKFYBVXBUHHZMW-HXWWIQRWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 82 86 0 0 0 0 0 0 0 0999 V2000 5.3386 1.5221 2.4526 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4091 1.4176 1.2281 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1961 2.8463 0.7748 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2034 0.7409 0.1536 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0804 -0.7331 0.2073 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6581 -1.2415 0.0978 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8199 -2.7390 0.4800 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2499 -1.2524 -1.3248 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8053 -1.4190 -1.6282 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9004 -0.5520 -0.7353 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0122 0.7937 -1.3604 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3316 1.3114 -1.3991 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3897 -0.7335 0.6144 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5535 -1.0883 1.5608 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8939 -1.3445 1.4398 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2994 -0.4769 0.2609 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7559 -0.3095 0.3035 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5631 -1.5224 0.6738 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0560 0.6866 1.4440 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0772 1.6978 1.1212 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1968 1.3170 0.2312 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6461 0.7438 -1.0411 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5290 -0.3524 -1.6229 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7186 1.8779 -2.0836 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2242 0.3748 -0.9372 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7314 -0.4951 -2.0790 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2062 -0.3729 -2.1251 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5655 -0.9783 -0.9072 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6490 -2.4820 -1.0962 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9237 2.5112 -0.0211 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7928 -0.5569 1.0790 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1088 0.8103 1.5559 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3410 1.7471 2.0682 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0114 2.4222 3.0515 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3146 0.6103 3.0589 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5166 3.5933 1.5330 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6585 3.0561 -0.2226 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1083 2.9905 0.6236 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0081 1.1540 -0.8585 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3001 0.9702 0.3152 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5613 -1.0840 1.1650 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6520 -1.2071 -0.6088 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6489 -3.1934 -0.1046 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0866 -2.8370 1.5440 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9055 -3.3031 0.1944 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7663 -0.4179 -1.8432 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7534 -2.1445 -1.8238 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5264 -2.4793 -1.6111 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7231 -1.0915 -2.7001 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3064 1.5438 -1.0369 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8572 0.6231 -2.4466 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2870 2.0954 -2.0047 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9069 -1.2337 2.6103 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4880 -1.0298 2.3014 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1224 -2.4138 1.2588 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8656 0.5512 0.4804 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5623 -1.2202 1.1214 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8146 -2.2026 -0.1261 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0650 -2.0205 1.5256 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3297 0.1492 2.3862 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1166 1.2506 1.7257 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6285 2.6478 0.7087 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5313 2.0359 2.1005 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9692 0.6601 0.7090 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9880 -0.8147 -2.4585 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9233 -1.0376 -0.8728 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4305 0.1681 -2.0604 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9536 2.6350 -1.7386 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4400 1.5360 -3.0803 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6821 2.4001 -2.0313 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6149 1.3237 -1.0143 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1036 -1.5087 -2.0734 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0858 -0.0043 -3.0072 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9348 -0.8674 -3.0696 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0808 0.7330 -2.1620 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3874 -2.7721 -2.1348 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7110 -2.8382 -1.0089 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0019 -3.0560 -0.4312 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4409 2.7148 0.8155 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9742 -1.1874 2.0232 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0271 0.8906 2.6937 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2171 1.4612 1.2956 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 1 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 6 11 12 1 0 10 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 21 30 1 0 13 31 1 0 31 32 1 0 32 2 1 0 31 6 1 0 28 10 1 0 28 16 1 0 25 17 1 0 1 33 1 0 1 34 1 0 1 35 1 0 3 36 1 0 3 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 7 43 1 0 7 44 1 0 7 45 1 0 8 46 1 0 8 47 1 0 9 48 1 0 9 49 1 0 11 50 1 0 11 51 1 0 12 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 16 56 1 1 18 57 1 0 18 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 20 62 1 0 20 63 1 0 21 64 1 1 23 65 1 0 23 66 1 0 23 67 1 0 24 68 1 0 24 69 1 0 24 70 1 0 25 71 1 6 26 72 1 0 26 73 1 0 27 74 1 0 27 75 1 0 29 76 1 0 29 77 1 0 29 78 1 0 30 79 1 0 31 80 1 1 32 81 1 0 32 82 1 0 M END

Standard InCHIKey	VKFYBVXBUHHZMW-HXWWIQRWSA-N
Standard InCHI	InChI=1S/C30H50O2/c1-25(2)14-15-27(5)16-17-30(19-31)20(21(27)18-25)8-9-23-28(6)12-11-24(32)26(3,4)22(28)10-13-29(23,30)7/h8,21-24,31-32H,9-19H2,1-7H3/t21-,22-,23+,24+,27+,28-,29+,30-/m0/s1
SMILES	CC1(C)CC[C@]2(C)CC[C@]3(CO)C(=CC[C@@H]4[C@@]5(C)CC[C@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]2C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	442.38	Volume:	499.598 ? Van der Waals volume.
Dense:	0.885	LogP:	4.965 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.431 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.447 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	26.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.424	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.749	Fsp³:	0.933
MCE-18:	102.207 ? 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:	0.827	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.632	Promiscuous compounds:	0.114

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.27	MDCK Permeability:	-4.941
Pgp-inhibitor:	0.908	Pgp-substrate:	0.05
PAMPA:	0.915 ? 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):	0.0
20% Bioavailability (F20%):	0.448	30% Bioavailability (F30%):	0.413
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.902	MRP1:	0.872
Plasma Protein Binding (PPB):	94.53%	Volume Distribution (VD):	0.06
Fu:	5.34% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.857	BCRP inhibitor:	0.29
BSEP inhibitor:	0.991

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.816
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.736
CYP2C9-inhibitor:	0.036	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.921	CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.03
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.635
HLM stability:	0.975 ? 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):

10.904

Half-life (T1/2):

0.583

ADMET: Toxicity

hERG Blockers:	0.045	hERG Blockers (10um):	0.186
Human Hepatotoxicity (H-HT):	0.486	Drug-induced Liver Injury (DILI):	0.091
AMES Toxicity:	0.385	Rat Oral Acute Toxicity:	0.286
Maximum Recommended Daily Dose:	0.534	Skin Sensitization:	0.875
Carcinogencity:	0.871	Eye Corrosion:	0.011
Eye Irritation:	0.587	Respiratory Toxicity:	0.845
Drug-induced Neurotoxicity:	0.059	Ototoxicity:	0.596
Hematotoxicity:	0.432	Drug-induced Nephrotoxicity:	0.667
Genotoxicity:	0.421	RPMI-8226 Immunitoxicity:	0.078
A549 Cytotoxicity:	0.256	Hek293 Cytotoxicity:	0.37
BCF:	2.296 ? 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:	4.335 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.462 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.053 ? 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
NPO13182	Achillea wilhelmsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38783072]
NPO13182	Achillea wilhelmsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39349567]
NPO17373.1	Cunninghamia lanceolata var. konishii	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3990	Acacia salicina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3446	Acanthaster planci	Species	Acanthasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13182	Achillea wilhelmsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16254	Backhousia angustifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6746	Blighia welwitschii	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17030	Calvatia lilacina	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10438	Tanacetum nubigenum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17707	Dioscorea villosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18768	Haliclona tubifera	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2591	Io fluvialis	Species	Pleuroceridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16377	Juniperus ashei	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9524	Kalanchoe blossfeldiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18031	Russula vesca	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15966	Sassafras officinalis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23695	Setosphaeria turcica	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17030	Calvatia lilacina	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2591	Io fluvialis	Species	Pleuroceridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3446	Acanthaster planci	Species	Acanthasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18031	Russula vesca	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16254	Backhousia angustifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15966	Sassafras officinalis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23695	Setosphaeria turcica	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17030	Calvatia lilacina	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3990	Acacia salicina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10438	Tanacetum nubigenum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9524	Kalanchoe blossfeldiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13182	Achillea wilhelmsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16377	Juniperus ashei	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18768	Haliclona tubifera	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6746	Blighia welwitschii	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17373.1	Cunninghamia lanceolata var. konishii	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17707	Dioscorea villosa	Species	Dioscoreaceae	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 NPC225779 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	25156
0.1-0.2	20003
0.2-0.3	3652
0.3-0.4	805
0.4-0.5	174
0.5-0.6	41
0.6-0.7	11
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	Natural Product ID
0.7885	Intermediate Similarity	NPC290598
0.7885	Intermediate Similarity	NPC30590
0.7273	Intermediate Similarity	NPC474989
0.7193	Intermediate Similarity	NPC470588
0.7143	Intermediate Similarity	NPC101475
0.7143	Intermediate Similarity	NPC196753
0.7018	Intermediate Similarity	NPC253807
0.7018	Intermediate Similarity	NPC158662
0.7018	Intermediate Similarity	NPC480924
0.661	Remote Similarity	NPC53744
0.6552	Remote Similarity	NPC311078
0.6552	Remote Similarity	NPC34177
0.6441	Remote Similarity	NPC235341
0.6333	Remote Similarity	NPC238992
0.619	Remote Similarity	NPC198664
0.6129	Remote Similarity	NPC246708
0.6034	Remote Similarity	NPC27765
0.6034	Remote Similarity	NPC122418
0.6034	Remote Similarity	NPC491014
0.6	Remote Similarity	NPC237344
0.5846	Remote Similarity	NPC488519
0.5806	Remote Similarity	NPC159168
0.5692	Remote Similarity	NPC274330
0.5645	Remote Similarity	NPC40394
0.5645	Remote Similarity	NPC475862
0.5645	Remote Similarity	NPC478657
0.5588	Remote Similarity	NPC480919
0.5507	Remote Similarity	NPC294360
0.55	Remote Similarity	NPC601696
0.5469	Remote Similarity	NPC480950
0.5455	Remote Similarity	NPC480946
0.5455	Remote Similarity	NPC130577
0.5455	Remote Similarity	NPC142415
0.5455	Remote Similarity	NPC102683
0.5373	Remote Similarity	NPC171203
0.5373	Remote Similarity	NPC307426
0.5373	Remote Similarity	NPC98442
0.5373	Remote Similarity	NPC242468
0.5342	Remote Similarity	NPC480920
0.5312	Remote Similarity	NPC230295
0.5312	Remote Similarity	NPC98386
0.5303	Remote Similarity	NPC17733
0.5303	Remote Similarity	NPC470629
0.5278	Remote Similarity	NPC273668
0.5246	Remote Similarity	NPC120098
0.5238	Remote Similarity	NPC132478
0.5224	Remote Similarity	NPC2539
0.5161	Remote Similarity	NPC142754
0.5147	Remote Similarity	NPC182797
0.5147	Remote Similarity	NPC51700
0.5147	Remote Similarity	NPC88716
0.5147	Remote Similarity	NPC68160
0.5147	Remote Similarity	NPC52169
0.5147	Remote Similarity	NPC488562
0.5135	Remote Similarity	NPC480921
0.5132	Remote Similarity	NPC167383
0.5085	Remote Similarity	NPC138374
0.5085	Remote Similarity	NPC472805
0.5085	Remote Similarity	NPC34700
0.5085	Remote Similarity	NPC90979
0.5077	Remote Similarity	NPC95594

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC225779 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7959
0.1-0.2	1138
0.2-0.3	48
0.3-0.4	4
0.4-0.5	0
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
0.5147	Remote Similarity	NPD7645	Phase 2

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