NPASS Compound

Natural Product: NPC65172

Natural Product ID	NPC65172
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RQTXEZTYXQREQG-FLHZBHLPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21591252
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

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 100107 0 0 0 0 0 0 0 0999 V2000 5.4078 0.6537 -2.4362 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1557 0.4078 -0.9740 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8984 -0.3489 -0.7012 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8894 -0.8576 0.7195 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7511 -0.0695 1.3738 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7802 -0.1188 0.2489 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3327 -1.5233 0.0294 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5838 0.7603 0.3890 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0990 0.3523 1.6731 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5354 0.8616 1.6967 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2235 0.0896 0.5916 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6922 0.2504 0.7343 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1345 -0.6060 1.9293 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1094 1.6681 1.0696 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4767 -0.2705 -0.4508 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8521 0.1568 -1.7615 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3927 -0.2324 -1.8143 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6744 0.5485 -0.7056 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2044 1.8962 -0.9888 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2351 0.6888 -0.8274 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4077 0.1693 -2.0585 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8633 0.0852 -2.1310 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6433 0.4064 -0.9080 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7864 1.9011 -0.8257 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7580 0.2239 -0.3912 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7389 -0.7564 -0.2929 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5564 -0.5007 0.9530 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0273 -0.6458 0.6292 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4169 0.3182 -0.4618 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2579 0.5356 -1.4335 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5199 -0.6454 -1.4473 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5197 -0.2213 -1.1479 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7634 -0.4018 1.7896 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2766 -1.4314 1.9568 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0257 -0.6098 1.4258 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0850 -1.2032 0.7253 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3649 -0.3020 -0.4307 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2737 0.6142 0.1070 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1654 -0.1312 0.8639 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0975 -0.8953 -0.0356 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8814 0.6806 1.8999 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3173 -1.1633 1.6027 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0134 -0.7631 2.8845 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7697 -2.5014 0.3227 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6965 1.7411 -2.5482 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5963 0.3560 -3.0970 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3239 0.1067 -2.8117 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0816 1.3798 -0.4057 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8893 -1.2239 -1.4159 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6812 -1.9514 0.7677 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1503 0.9111 1.6279 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3974 -0.5784 2.2929 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7940 -2.0295 -0.8365 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6317 -2.1492 0.9192 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2081 -1.6334 0.0134 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9183 1.8262 0.5522 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4828 0.7483 2.5290 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1542 -0.7461 1.8106 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9236 0.6537 2.6978 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5856 1.9572 1.5480 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9821 -0.9932 0.7794 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5579 -1.5839 1.5773 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9236 -0.1209 2.5066 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2593 -0.8755 2.5526 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5867 2.3626 0.3901 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8844 1.9157 2.1158 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1928 1.7491 0.8164 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4934 -1.3956 -0.4055 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4197 -0.3071 -2.5720 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9170 1.2463 -1.8341 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2315 -1.3073 -1.5905 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0038 0.0401 -2.8118 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1249 2.7182 -0.2864 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3245 2.2417 -2.0574 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0007 0.7557 -2.9366 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0213 -0.8630 -2.2414 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2425 0.7809 -2.9395 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2171 -0.9260 -2.4941 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5444 2.1928 -1.5901 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8223 2.3351 -1.2027 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1032 2.2925 0.1361 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3525 -1.7774 -0.2739 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3277 0.5204 1.3523 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1925 -1.6832 0.2984 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6924 1.3261 -0.0573 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7044 0.6862 -2.4294 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6713 1.4024 -1.0765 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9951 -0.8147 -0.5164 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1583 -0.2120 2.5601 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2832 -0.9669 2.8425 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9246 -0.8226 -1.2560 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0317 -1.1681 0.5264 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3435 -0.2725 -0.9026 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6238 -1.8327 -0.4117 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9557 0.4349 1.9938 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7544 1.7741 1.6941 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4529 0.5305 2.9284 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8325 -2.1408 1.6589 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1395 -1.0938 3.2115 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0955 -2.5855 -0.6272 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 6 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 12 15 1 0 15 16 1 0 16 17 1 0 18 17 1 6 18 19 1 0 20 19 1 6 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 1 15 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 28 33 1 0 27 34 1 0 4 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 39 41 1 0 39 42 1 0 42 43 1 0 36 44 1 6 37 2 1 0 23 3 1 0 31 26 1 0 42 36 1 0 23 6 1 0 20 8 1 0 18 11 1 0 20 18 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 1 3 49 1 6 4 50 1 6 5 51 1 0 5 52 1 0 7 53 1 0 7 54 1 0 7 55 1 0 8 56 1 1 9 57 1 0 9 58 1 0 10 59 1 0 10 60 1 0 11 61 1 1 13 62 1 0 13 63 1 0 13 64 1 0 14 65 1 0 14 66 1 0 14 67 1 0 15 68 1 6 16 69 1 0 16 70 1 0 17 71 1 0 17 72 1 0 19 73 1 0 19 74 1 0 21 75 1 0 21 76 1 0 22 77 1 0 22 78 1 0 24 79 1 0 24 80 1 0 24 81 1 0 26 82 1 1 27 83 1 1 28 84 1 6 29 85 1 1 30 86 1 0 30 87 1 0 32 88 1 0 33 89 1 0 34 90 1 0 37 91 1 6 40 92 1 0 40 93 1 0 40 94 1 0 41 95 1 0 41 96 1 0 41 97 1 0 42 98 1 1 43 99 1 0 44100 1 0 M END

Standard InCHIKey	RQTXEZTYXQREQG-FLHZBHLPSA-N
Standard InCHI	InChI=1S/C35H56O9/c1-17-23-19(43-35(40)26(17)44-30(4,5)28(35)39)14-32(7)21-9-8-20-29(2,3)22(42-27-25(38)24(37)18(36)15-41-27)10-11-33(20)16-34(21,33)13-12-31(23,32)6/h17-28,36-40H,8-16H2,1-7H3/t17-,18+,19-,20-,21-,22-,23-,24-,25+,26+,27-,28+,31+,32-,33+,34-,35-/m0/s1
SMILES	C[C@H]1[C@H]2[C@H](C[C@@]3(C)[C@@H]4CC[C@H]5C(C)(C)[C@H](CC[C@]65C[C@@]46CC[C@]23C)O[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)O[C@]2([C@@H]1OC(C)(C)[C@H]2O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	620.39	Volume:	624.576 ? Van der Waals volume.
Dense:	0.993	LogP:	1.598 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.129 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.388 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	37.0
TPSA:	138.07 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	5.0	Rings:	8.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.295	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.588	Fsp³:	1.0
MCE-18:	216.6 ? 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:	0.82	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? 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:	0.149	Promiscuous compounds:	0.029

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.664	MDCK Permeability:	-5.117
Pgp-inhibitor:	0.001	Pgp-substrate:	0.773
PAMPA:	0.992 ? 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%):	0.043	30% Bioavailability (F30%):	0.102
50% Bioavailability (F50%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.219	MRP1:	0.125
Plasma Protein Binding (PPB):	72.354%	Volume Distribution (VD):	-0.294
Fu:	24.243% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.786
BSEP inhibitor:	0.723

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.152	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.993	CYP3A4-substrate:	0.261
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.174
HLM stability:	0.159 ? 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):

4.704

Half-life (T1/2):

2.204

ADMET: Toxicity

hERG Blockers:	0.036	hERG Blockers (10um):	0.301
Human Hepatotoxicity (H-HT):	0.288	Drug-induced Liver Injury (DILI):	0.07
AMES Toxicity:	0.532	Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.18	Skin Sensitization:	0.997
Carcinogencity:	0.07	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.261
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.972
Hematotoxicity:	0.346	Drug-induced Nephrotoxicity:	0.52
Genotoxicity:	0.117	RPMI-8226 Immunitoxicity:	0.148
A549 Cytotoxicity:	0.061	Hek293 Cytotoxicity:	0.201
BCF:	2.998 ? 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:	4.949 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.788 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.777 ? 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
NPO21656	Pholidota yunnanensis	Species	Orchidaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16394543]
NPO22504	Tovomita longifolia	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16562847]
NPO30451	Cimicifuga simplex	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17503850]
NPO30451	Cimicifuga simplex	n.a.	n.a.	n.a.	aerial parts	n.a.	n.a.	PMID[20184336]
NPO20204	Tephrosia candida	Species	Fabaceae	Eukaryota	aerial parts	Limbe (South West) Province, Cameroon	2007-APR	PMID[21510635]
NPO20204	Tephrosia candida	Species	Fabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21510635]
NPO21417	Cortinarius evernius	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20898	Agaricus bisporus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20204	Tephrosia candida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23102	Siphonaria pectinata	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30451	Cimicifuga simplex	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26301	Acanthopanax brachypus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22374	Anomala albopilosa	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20024	Antennaria cana	Species	Carabidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19967	Calophyllum tomentosum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31350	Cimicifuga acerina	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4213	Dicranopteris linearis	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21346	Eriocaulon buergerianum	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22959	Eriococcus coriaceus	Species	Eriococcidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22633	Ganoderma carnosum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22442	Helix pomatia	Species	Helicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21855	Hydrallmania falcata	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13770	Neurospora santi-florii	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20459	Pfaffia pulverulenta	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21656	Pholidota yunnanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22702	Phytolacca dioica	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22310	Pseudodistoma obscurum	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20970	Salvia melissodora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21987	Senecio hygrophilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22504	Tovomita longifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20898	Agaricus bisporus	Species	Agaricaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20898	Agaricus bisporus	Species	Agaricaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21656	Pholidota yunnanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20898	Agaricus bisporus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30451	Cimicifuga simplex	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO19967	Calophyllum tomentosum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31350	Cimicifuga acerina	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO21656	Pholidota yunnanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19967	Calophyllum tomentosum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22702	Phytolacca dioica	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21346	Eriocaulon buergerianum	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20898	Agaricus bisporus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20898	Agaricus bisporus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30451	Cimicifuga simplex	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21346	Eriocaulon buergerianum	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31350	Cimicifuga acerina	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21346	Eriocaulon buergerianum	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22633	Ganoderma carnosum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4213	Dicranopteris linearis	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22702	Phytolacca dioica	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20204	Tephrosia candida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22310	Pseudodistoma obscurum	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20024	Antennaria cana	Species	Carabidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21855	Hydrallmania falcata	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21346	Eriocaulon buergerianum	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23102	Siphonaria pectinata	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21417	Cortinarius evernius	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26301	Acanthopanax brachypus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20459	Pfaffia pulverulenta	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21656	Pholidota yunnanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22504	Tovomita longifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20898	Agaricus bisporus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19967	Calophyllum tomentosum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22959	Eriococcus coriaceus	Species	Eriococcidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22374	Anomala albopilosa	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13770	Neurospora santi-florii	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22442	Helix pomatia	Species	Helicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20970	Salvia melissodora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21987	Senecio hygrophilus	Species	Asteraceae	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 NPC65172 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	21835
0.1-0.2	25034
0.2-0.3	2780
0.3-0.4	167
0.4-0.5	29
0.5-0.6	10
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	Natural Product ID
0.7973	Intermediate Similarity	NPC478613
0.7949	Intermediate Similarity	NPC472081
0.6988	Remote Similarity	NPC476835
0.561	Remote Similarity	NPC473726
0.5506	Remote Similarity	NPC472079
0.5402	Remote Similarity	NPC478630
0.5222	Remote Similarity	NPC475207
0.5213	Remote Similarity	NPC97260
0.5213	Remote Similarity	NPC476837
0.5161	Remote Similarity	NPC139181
0.5114	Remote Similarity	NPC476513
0.5111	Remote Similarity	NPC476510
0.5055	Remote Similarity	NPC476512

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC65172 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7343
0.1-0.2	1783
0.2-0.3	23
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
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
		NPD

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