NPASS Compound

Natural Product: NPC285044

Natural Product ID	NPC285044
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WXMARHKAXWRNDM-REQRAIAKSA-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:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

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 93 99 0 0 0 0 0 0 0 0999 V2000 9.9908 -0.3742 0.4909 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7345 -0.1043 1.3317 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1601 1.1940 0.8046 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3397 0.7796 -0.4271 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1696 0.0116 0.1171 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1823 -0.4109 -0.9573 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6714 -1.5865 -1.7487 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9801 -0.7075 -0.1091 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1546 0.3489 0.9970 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9796 1.3155 0.7580 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9622 0.3594 0.3197 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6637 0.8837 -0.1959 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1554 2.0504 0.5578 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3132 2.1453 0.4667 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1399 1.2542 -0.0334 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5931 1.5285 -0.0357 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2274 0.5281 0.9345 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3811 -0.7115 1.1080 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6035 -1.0930 -0.1282 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6597 -0.0203 -0.5938 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7532 -0.0144 -2.1272 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2365 -0.3235 -0.2561 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3761 -1.3106 -1.2276 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7861 -1.6608 -0.9293 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6636 -0.4300 -0.7603 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7926 0.2726 -2.0648 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4938 0.1599 0.5907 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4723 0.4789 1.5071 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4692 1.4958 1.0911 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7105 0.9413 0.4394 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1710 -0.3395 1.0483 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9500 -1.2091 1.2775 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3687 -1.7329 0.0115 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3804 -2.6668 0.3399 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0705 -0.5881 2.1389 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8833 -0.1319 2.2067 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5858 0.7675 -0.9345 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9233 2.2364 2.2134 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3604 0.9591 0.7836 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4747 -0.9487 1.0248 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7843 -1.2411 1.2355 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3680 0.5715 0.0399 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7352 -1.0480 -0.3580 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8029 -0.8144 1.1046 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1382 0.0410 2.3775 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4168 1.5630 1.5415 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9410 1.9162 0.5559 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9948 1.7322 -0.8804 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9405 0.2420 -1.1607 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0460 0.5145 -1.5913 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1020 -2.5121 -1.5675 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6695 -1.4161 -2.8458 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7367 -1.7495 -1.4722 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0843 -1.7147 0.2964 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0106 -0.0976 1.9829 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3280 2.0323 -0.0018 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7756 1.8819 1.6805 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7527 -0.3554 1.1527 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7682 1.2164 -1.2732 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4455 1.8976 1.6334 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6610 2.9561 0.1482 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7430 3.0937 0.8766 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0509 1.4588 -1.0431 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7640 2.5691 0.3008 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1765 1.0512 1.9298 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0720 -1.5538 1.3174 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7274 -0.6604 2.0100 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3531 -1.3708 -0.8969 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0381 -2.0020 0.1082 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7746 0.3565 -2.4363 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9893 0.6064 -2.5892 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7404 -1.0816 -2.4305 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2143 -0.8058 0.7446 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2042 -2.2811 -1.2200 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2889 -0.9500 -2.2750 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8123 -2.2730 0.0070 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1690 -2.3077 -1.7268 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2015 1.2900 -1.9982 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5403 -0.3236 -2.6706 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8816 0.2558 -2.6716 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8778 0.9854 2.3517 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0642 2.2732 0.4088 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5165 1.7269 0.5527 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8339 -0.8895 0.3333 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3686 -2.1206 1.8191 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1826 -2.3606 -0.4725 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0433 -0.9549 -0.6786 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7575 -3.5294 0.5882 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9745 0.8509 2.3402 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0354 1.4729 -1.3595 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1399 2.3048 2.8256 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1943 -1.9943 0.4976 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8412 -1.7986 2.2207 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 17 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 29 38 1 0 9 39 1 0 5 40 1 1 40 41 1 0 41 2 1 0 39 5 1 0 25 8 1 0 35 28 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 1 3 46 1 0 3 47 1 0 4 48 1 0 4 49 1 0 6 50 1 6 7 51 1 0 7 52 1 0 7 53 1 0 8 54 1 1 9 55 1 1 10 56 1 0 10 57 1 0 11 58 1 1 12 59 1 6 13 60 1 0 13 61 1 0 14 62 1 0 16 63 1 0 16 64 1 0 17 65 1 1 18 66 1 0 18 67 1 0 19 68 1 0 19 69 1 0 21 70 1 0 21 71 1 0 21 72 1 0 22 73 1 1 23 74 1 0 23 75 1 0 24 76 1 0 24 77 1 0 26 78 1 0 26 79 1 0 26 80 1 0 28 81 1 1 29 82 1 6 30 83 1 6 31 84 1 6 32 85 1 1 33 86 1 0 33 87 1 0 34 88 1 0 36 89 1 0 37 90 1 0 38 91 1 0 41 92 1 0 41 93 1 0 M END

Standard InCHIKey	WXMARHKAXWRNDM-REQRAIAKSA-N
Standard InCHI	InChI=1S/C33H52O8/c1-17-7-12-33(38-16-17)18(2)26-24(41-33)14-23-21-6-5-19-13-20(8-10-31(19,3)22(21)9-11-32(23,26)4)39-30-29(37)28(36)27(35)25(15-34)40-30/h5,17-18,20-30,34-37H,6-16H2,1-4H3/t17-,18-,20-,21+,22-,23-,24-,25+,26-,27+,28-,29+,30+,31-,32-,33+/m0/s1
SMILES	C[C@H]1CC[C@@]2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC=C6C[C@H](CC[C@]6(C)[C@H]5CC[C@]34C)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	576.37	Volume:	587.114 ? Van der Waals volume.
Dense:	0.982	LogP:	4.012 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.976 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.771 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	36.0
TPSA:	117.84 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	4.0	Rings:	7.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.377	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.725	Fsp³:	0.939
MCE-18:	167.75 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.796	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? 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:	0.168	Promiscuous compounds:	0.009

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.674	MDCK Permeability:	-5.051
Pgp-inhibitor:	0.009	Pgp-substrate:	0.145
PAMPA:	0.514 ? 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%):	0.01	30% Bioavailability (F30%):	0.68
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016	MRP1:	0.016
Plasma Protein Binding (PPB):	73.707%	Volume Distribution (VD):	-0.341
Fu:	26.267% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.955
BSEP inhibitor:	0.824

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.023	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	0.997	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.988
HLM stability:	0.227 ? 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):

5.141

Half-life (T1/2):

1.797

ADMET: Toxicity

hERG Blockers:	0.082	hERG Blockers (10um):	0.241
Human Hepatotoxicity (H-HT):	0.524	Drug-induced Liver Injury (DILI):	0.924
AMES Toxicity:	0.7	Rat Oral Acute Toxicity:	0.081
Maximum Recommended Daily Dose:	0.262	Skin Sensitization:	1.0
Carcinogencity:	0.486	Eye Corrosion:	0.0
Eye Irritation:	0.015	Respiratory Toxicity:	0.018
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	0.941
Hematotoxicity:	0.166	Drug-induced Nephrotoxicity:	0.412
Genotoxicity:	0.009	RPMI-8226 Immunitoxicity:	0.153
A549 Cytotoxicity:	0.586	Hek293 Cytotoxicity:	0.78
BCF:	2.385 ? 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:	3.808 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.86 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.456 ? 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
NPO17509	Gentiana bellidifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4020(01)98434-0]
NPO12113	Aconitum forrestii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1021/np50033a013]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	Sarawak, Malaysia	n.a.	PMID[11430019]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1379639]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17827771]
NPO14832	Calocedrus macrolepis	Species	Cupressaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18206367]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18681480]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18681480]
NPO19447	Daphniphyllum subverticillatum	Species	Daphniphyllaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19739650]
NPO18442	Capsicum baccatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21535519]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO11662	Solanum virginianum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39081888]
NPO18682	Piper puberulum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623032]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8792623]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9099	Carissa spinarum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19377	Podocarpus blumei	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13433	Adenium obesum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11331	Phellinus tremulae	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12113	Aconitum forrestii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2708	Agaricus nebularis	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8770	Euphorbia wallichii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18778	Paullinia pinnata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19525	Tephrosia bracteolata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18361	Mollugo cerviana	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16571	Canarium muelleri	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19447	Daphniphyllum subverticillatum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14266	Borassus flabellifer	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15183	Salvia horminum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18064	Lycopodium paniculatum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15880	Microlepia marginata	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17648	Subergorgia hicksoni	Species	Subergorgiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18608	Fagopyrum cymosum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15880	Microlepia marginata	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8770	Euphorbia wallichii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18682	Piper puberulum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18608	Fagopyrum cymosum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12113	Aconitum forrestii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15880	Microlepia marginata	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8770	Euphorbia wallichii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11662	Solanum virginianum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12113	Aconitum forrestii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16148	Neoboutonia glabrescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13433	Adenium obesum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18608	Fagopyrum cymosum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18682	Piper puberulum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18608	Fagopyrum cymosum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16148	Neoboutonia glabrescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18940	Selinum papyraceum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19314	Albizia schimperana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12113	Aconitum forrestii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18608	Fagopyrum cymosum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18272	Mikania oblongifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8770	Euphorbia wallichii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18064	Lycopodium paniculatum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20860	Lygodium pinnatifidum	Species	Lygodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18361	Mollugo cerviana	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15880	Microlepia marginata	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19377	Podocarpus blumei	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17648	Subergorgia hicksoni	Species	Subergorgiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11331	Phellinus tremulae	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15183	Salvia horminum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13433	Adenium obesum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18682	Piper puberulum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9099	Carissa spinarum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27385	Calamus insignis	Species	Sparidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19842	Sideritis condensata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10175	Anaptychia obscura	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16571	Canarium muelleri	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17509	Gentiana bellidifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18442	Capsicum baccatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2708	Agaricus nebularis	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14832	Calocedrus macrolepis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18778	Paullinia pinnata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17793	Parkia javanica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16274	Calonectria lauri	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11662	Solanum virginianum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19098	Hypotrachyna quaesita	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22826	Buxus rolfei	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19447	Daphniphyllum subverticillatum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19722	Tephrosia odorata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18540	Berkheya radula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13869	Ranunculus bulbosus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19525	Tephrosia bracteolata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19249	Garcinia latissima	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18860	Pelea madagascarica	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14266	Borassus flabellifer	Species	Arecaceae	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 NPC285044 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	21503
0.1-0.2	23617
0.2-0.3	3798
0.3-0.4	662
0.4-0.5	119
0.5-0.6	85
0.6-0.7	40
0.7-0.8	0
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC181845
0.8295	Intermediate Similarity	NPC477809
0.8256	Intermediate Similarity	NPC113044
0.8256	Intermediate Similarity	NPC283829
0.8256	Intermediate Similarity	NPC14704
0.8256	Intermediate Similarity	NPC161676
0.8235	Intermediate Similarity	NPC470432
0.8235	Intermediate Similarity	NPC230507
0.8	Intermediate Similarity	NPC300557
0.7912	Intermediate Similarity	NPC480555
0.7912	Intermediate Similarity	NPC150372
0.7778	Intermediate Similarity	NPC602423
0.7609	Intermediate Similarity	NPC6806
0.7582	Intermediate Similarity	NPC470433
0.7582	Intermediate Similarity	NPC46190
0.7582	Intermediate Similarity	NPC171073
0.7449	Intermediate Similarity	NPC477811
0.7292	Intermediate Similarity	NPC475550
0.7273	Intermediate Similarity	NPC480553
0.7113	Intermediate Similarity	NPC269297
0.7113	Intermediate Similarity	NPC222202
0.7071	Intermediate Similarity	NPC480554
0.7041	Intermediate Similarity	NPC475333
0.7041	Intermediate Similarity	NPC224098
0.7041	Intermediate Similarity	NPC309278
0.7041	Intermediate Similarity	NPC208383
0.697	Remote Similarity	NPC194207
0.697	Remote Similarity	NPC22779
0.6962	Remote Similarity	NPC100451
0.6947	Remote Similarity	NPC248746
0.686	Remote Similarity	NPC485594
0.6792	Remote Similarity	NPC477808
0.6709	Remote Similarity	NPC235126
0.6709	Remote Similarity	NPC242419
0.6705	Remote Similarity	NPC325828
0.6635	Remote Similarity	NPC232054
0.6629	Remote Similarity	NPC234352
0.6604	Remote Similarity	NPC480556
0.6596	Remote Similarity	NPC141433
0.6531	Remote Similarity	NPC249553
0.6531	Remote Similarity	NPC42171
0.6531	Remote Similarity	NPC182900
0.6526	Remote Similarity	NPC305423
0.6517	Remote Similarity	NPC297348
0.6517	Remote Similarity	NPC249204
0.6517	Remote Similarity	NPC48339
0.6517	Remote Similarity	NPC141769
0.6517	Remote Similarity	NPC477547
0.6471	Remote Similarity	NPC277715
0.6389	Remote Similarity	NPC224314
0.6381	Remote Similarity	NPC31896
0.6344	Remote Similarity	NPC107188
0.6237	Remote Similarity	NPC206003
0.6237	Remote Similarity	NPC473610
0.6214	Remote Similarity	NPC32361
0.6214	Remote Similarity	NPC13193
0.6211	Remote Similarity	NPC107962
0.6196	Remote Similarity	NPC477451
0.617	Remote Similarity	NPC306131
0.617	Remote Similarity	NPC211354
0.617	Remote Similarity	NPC200802
0.6145	Remote Similarity	NPC486119
0.6071	Remote Similarity	NPC22140
0.6071	Remote Similarity	NPC243728
0.6071	Remote Similarity	NPC158088
0.6067	Remote Similarity	NPC24960
0.5982	Remote Similarity	NPC210569
0.5979	Remote Similarity	NPC6295
0.5946	Remote Similarity	NPC477807
0.593	Remote Similarity	NPC282669
0.5914	Remote Similarity	NPC294686
0.59	Remote Similarity	NPC42482
0.59	Remote Similarity	NPC98696
0.59	Remote Similarity	NPC40440
0.5859	Remote Similarity	NPC160426
0.5826	Remote Similarity	NPC305771
0.5826	Remote Similarity	NPC94072
0.5826	Remote Similarity	NPC169816
0.5806	Remote Similarity	NPC177834
0.58	Remote Similarity	NPC475351
0.5789	Remote Similarity	NPC250393
0.5758	Remote Similarity	NPC70204
0.5714	Remote Similarity	NPC295980
0.567	Remote Similarity	NPC19400
0.5652	Remote Similarity	NPC296686
0.5647	Remote Similarity	NPC177818
0.5625	Remote Similarity	NPC222731
0.5619	Remote Similarity	NPC97700
0.5619	Remote Similarity	NPC73243
0.5619	Remote Similarity	NPC244086
0.5619	Remote Similarity	NPC184617
0.5619	Remote Similarity	NPC84956
0.5619	Remote Similarity	NPC30856
0.5619	Remote Similarity	NPC102016
0.5619	Remote Similarity	NPC95051
0.5618	Remote Similarity	NPC144790
0.5618	Remote Similarity	NPC149400
0.5588	Remote Similarity	NPC161738
0.5565	Remote Similarity	NPC15918
0.5543	Remote Similarity	NPC242748
0.5524	Remote Similarity	NPC128572
0.5524	Remote Similarity	NPC475182
0.5514	Remote Similarity	NPC247037
0.55	Remote Similarity	NPC125324
0.55	Remote Similarity	NPC94272
0.55	Remote Similarity	NPC485595
0.5446	Remote Similarity	NPC195297
0.5429	Remote Similarity	NPC124677
0.5424	Remote Similarity	NPC263359
0.5364	Remote Similarity	NPC218571
0.5364	Remote Similarity	NPC487615
0.5364	Remote Similarity	NPC249265
0.5347	Remote Similarity	NPC15249
0.5347	Remote Similarity	NPC25455
0.5333	Remote Similarity	NPC92890
0.5327	Remote Similarity	NPC294129
0.5315	Remote Similarity	NPC23808
0.5315	Remote Similarity	NPC87998
0.5312	Remote Similarity	NPC272015
0.5294	Remote Similarity	NPC207617
0.5294	Remote Similarity	NPC607440
0.5288	Remote Similarity	NPC473601
0.5269	Remote Similarity	NPC481420
0.5269	Remote Similarity	NPC473774
0.5269	Remote Similarity	NPC481419
0.5269	Remote Similarity	NPC481417
0.5269	Remote Similarity	NPC481421
0.5268	Remote Similarity	NPC132080
0.5253	Remote Similarity	NPC121453
0.5238	Remote Similarity	NPC475643
0.5234	Remote Similarity	NPC150057
0.5234	Remote Similarity	NPC147753
0.52	Remote Similarity	NPC54619
0.5182	Remote Similarity	NPC475625
0.5176	Remote Similarity	NPC187159
0.5167	Remote Similarity	NPC244431
0.5152	Remote Similarity	NPC86020
0.5143	Remote Similarity	NPC486388
0.514	Remote Similarity	NPC51172
0.514	Remote Similarity	NPC49032
0.5135	Remote Similarity	NPC63609
0.5114	Remote Similarity	NPC473890
0.5109	Remote Similarity	NPC88962
0.5102	Remote Similarity	NPC131693
0.5102	Remote Similarity	NPC475436
0.5088	Remote Similarity	NPC308140
0.506	Remote Similarity	NPC248944
0.506	Remote Similarity	NPC7479
0.506	Remote Similarity	NPC257296
0.5049	Remote Similarity	NPC306991
0.5045	Remote Similarity	NPC116756

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC285044 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7160
0.1-0.2	1854
0.2-0.3	119
0.3-0.4	10
0.4-0.5	3
0.5-0.6	3
0.6-0.7	1
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
0.6705	Remote Similarity	NPD8171	Phase 2
0.5979	Remote Similarity	NPD8170	Phase 2
0.5234	Remote Similarity	NPD8450	Suspended
0.506	Remote Similarity	NPD6928	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