NPASS Compound

Natural Product: NPC130011

Natural Product ID	NPC130011
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2Alpha-Hydroxyfriedelan-3-One
IUPAC Name	(2R,4R,4aS,6aS,6aS,6bR,8aR,12aR,14aS,14bS)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1H-picen-3-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL450831
PubChem CID	21596125
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 5.2500 2.6261 -2.3427 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9194 1.4068 -1.7064 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4298 1.2094 -1.6647 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9028 0.5584 -0.4519 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8858 -0.0906 0.4603 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8300 1.0486 0.8916 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5215 1.4818 -0.3500 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6502 1.9277 -0.2702 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7663 0.6052 1.9698 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7239 -1.1593 -0.1039 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2175 -0.5543 1.7147 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9422 -1.3728 1.4517 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0443 -0.5134 0.6361 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6615 -0.3108 -0.7058 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9677 -1.5398 -1.4715 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7543 0.5368 -1.5791 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6532 0.0322 -1.5992 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2192 0.0746 -0.1725 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3969 -0.8892 0.6341 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5272 -2.3043 0.2251 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9719 -0.7535 2.0361 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4075 -1.1541 2.1287 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2888 -0.8116 0.9965 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6785 -0.4017 -0.2740 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4222 0.5755 -1.1173 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8056 0.9230 -0.7584 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9839 2.4431 -0.5739 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7947 0.5824 -1.8914 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3750 0.2944 0.4633 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3606 0.1587 1.5247 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1536 -2.0662 0.7158 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1785 1.4828 0.2652 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0469 2.5510 -2.8991 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4464 0.6292 -2.3106 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9835 2.2390 -1.8255 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1718 0.6863 -2.6320 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4587 1.3915 0.1852 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1632 1.8666 1.2722 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7578 -0.4716 2.1736 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8015 0.8668 1.6505 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5972 1.2147 2.9048 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8211 -1.0348 0.1417 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6739 -1.3336 -1.1719 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4647 -2.1452 0.3869 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8797 0.3183 2.3166 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8578 -1.2139 2.3344 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5640 -1.6011 2.4808 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2714 -2.3120 1.0316 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0975 0.4935 1.1557 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5935 -1.2390 -2.3596 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0330 -1.9295 -1.9437 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5032 -2.3361 -0.9821 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1435 0.4987 -2.6350 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8038 1.5764 -1.2739 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7722 -0.9552 -2.0497 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2562 0.7419 -2.1941 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0978 -2.9330 0.9693 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9536 -2.5244 -0.7480 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4820 -2.8177 0.2163 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4150 -1.3194 2.7987 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9128 0.3236 2.3684 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4115 -2.2626 2.3693 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7753 -0.7142 3.1093 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5686 -1.3317 -0.9176 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8369 1.5433 -1.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4293 0.2619 -2.2099 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0748 2.6100 -0.4768 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5246 3.0044 -1.3960 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5206 2.6776 0.4098 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8209 0.4814 -1.5071 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6675 1.3679 -2.6465 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4307 -0.4117 -2.2803 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8419 -0.6986 0.2794 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2133 0.9328 0.8613 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9741 1.0474 1.9875 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8434 -0.4328 2.3623 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4755 -2.0758 -0.3500 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9610 -2.1769 1.4347 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4841 -2.9416 0.8356 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4438 1.7751 1.0179 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0060 2.2015 -0.5948 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1550 1.8658 0.6911 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 7 8 2 0 6 9 1 0 5 10 1 6 5 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 26 29 1 0 29 30 1 0 23 31 1 6 18 32 1 1 7 2 1 0 19 13 1 0 30 23 1 0 14 4 1 0 24 18 1 0 1 33 1 0 2 34 1 6 3 35 1 0 3 36 1 0 4 37 1 1 6 38 1 1 9 39 1 0 9 40 1 0 9 41 1 0 10 42 1 0 10 43 1 0 10 44 1 0 11 45 1 0 11 46 1 0 12 47 1 0 12 48 1 0 13 49 1 1 15 50 1 0 15 51 1 0 15 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 20 57 1 0 20 58 1 0 20 59 1 0 21 60 1 0 21 61 1 0 22 62 1 0 22 63 1 0 24 64 1 6 25 65 1 0 25 66 1 0 27 67 1 0 27 68 1 0 27 69 1 0 28 70 1 0 28 71 1 0 28 72 1 0 29 73 1 0 29 74 1 0 30 75 1 0 30 76 1 0 31 77 1 0 31 78 1 0 31 79 1 0 32 80 1 0 32 81 1 0 32 82 1 0 M END

Standard InCHIKey	DSEKYWAQQVUQTP-XEWMWGOFSA-N
Standard InCHI	InChI=1S/C30H50O2/c1-19-24(32)20(31)17-22-27(19,5)10-9-21-28(22,6)14-16-30(8)23-18-25(2,3)11-12-26(23,4)13-15-29(21,30)7/h19-23,31H,9-18H2,1-8H3/t19-,20+,21-,22+,23+,26+,27+,28+,29+,30-/m0/s1
SMILES	O[C@@H]1C[C@@H]2[C@]([C@H](C1=O)C)(C)CC[C@H]1[C@@]2(C)CC[C@@]2([C@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	442.38	Volume:	499.598 ? Van der Waals volume.
Dense:	0.885	LogP:	4.574 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.158 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.584 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	27.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.423	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.957	Fsp³:	0.967
MCE-18:	105.763 ? 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:	0.802	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.609	Promiscuous compounds:	0.255

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.141	MDCK Permeability:	-4.875
Pgp-inhibitor:	0.984	Pgp-substrate:	0.001
PAMPA:	0.521 ? 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%):	0.476	30% Bioavailability (F30%):	0.077
50% Bioavailability (F50%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.738	MRP1:	0.889
Plasma Protein Binding (PPB):	96.928%	Volume Distribution (VD):	0.385
Fu:	4.328% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.528
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.08
CYP2C19-inhibitor:	0.998	CYP2C19-substrate:	0.712
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.927 ? 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):

11.026

Half-life (T1/2):

0.553

ADMET: Toxicity

hERG Blockers:	0.095	hERG Blockers (10um):	0.316
Human Hepatotoxicity (H-HT):	0.669	Drug-induced Liver Injury (DILI):	0.419
AMES Toxicity:	0.473	Rat Oral Acute Toxicity:	0.782
Maximum Recommended Daily Dose:	0.43	Skin Sensitization:	0.983
Carcinogencity:	0.939	Eye Corrosion:	0.151
Eye Irritation:	0.362	Respiratory Toxicity:	0.868
Drug-induced Neurotoxicity:	0.369	Ototoxicity:	0.414
Hematotoxicity:	0.723	Drug-induced Nephrotoxicity:	0.953
Genotoxicity:	0.929	RPMI-8226 Immunitoxicity:	0.146
A549 Cytotoxicity:	0.733	Hek293 Cytotoxicity:	0.731
BCF:	3.467 ? 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:	5.03 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.763 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.177 ? 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
NPO6850	Typha domingensis	Species	Typhaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21417376]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	Urup Island (4557,9 N; 15044,9 E; depth 66 m)	2008-AUG	PMID[21848268]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21848268]
NPO17226	Burkholderia pyrrocinia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[4955234]
NPO115	Eutreptia viridis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4293	Allium neapolitanum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2968	Anthopleura xanthogrammica	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17226	Burkholderia pyrrocinia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19333	Byssothecium obiones	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4816	Cycas armstrongii	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25775	Dasystenella acanthina	Species	Primnoidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1897	Ephedra aphylla	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6302	Licaria armeniaca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6130	Mammillaria magnimamma	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3756	Munronia delavayi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2609	Neonectria candida	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18463	Plectocephalus chilensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3419	Quercus suber	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO291	Suillus bovinus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10870	Trichilia hirta	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6850	Typha domingensis	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4816	Cycas armstrongii	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4293	Allium neapolitanum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6302	Licaria armeniaca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1897	Ephedra aphylla	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19333	Byssothecium obiones	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17226	Burkholderia pyrrocinia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3756	Munronia delavayi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2609	Neonectria candida	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO115	Eutreptia viridis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6130	Mammillaria magnimamma	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6850	Typha domingensis	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18463	Plectocephalus chilensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO291	Suillus bovinus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10870	Trichilia hirta	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25775	Dasystenella acanthina	Species	Primnoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3419	Quercus suber	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2968	Anthopleura xanthogrammica	Species	Actiniidae	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

Activity Type	# Activity
GI50	5
IC50	1

Activity Type	# Activity
Cell line	5
Non-molecular	1

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
NPT83	Cell line	MCF7	Homo sapiens	GI50	=	59500.0	nM	PMID[11678649]
NPT384	Cell line	TK-10	Homo sapiens	GI50	=	90500.0	nM	PMID[11678649]
NPT398	Cell line	UACC-62	Homo sapiens	GI50	=	86000.0	nM	PMID[11678649]
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	=	67800.0	nM	PMID[11678649]
NPT395	Cell line	SF-268	Homo sapiens	GI50	=	95800.0	nM	PMID[11678649]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	82300.0	nM	PMID[11678649]

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 NPC130011 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	24820
0.1-0.2	22581
0.2-0.3	2336
0.3-0.4	90
0.4-0.5	15
0.5-0.6	11
0.6-0.7	4
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
0.6429	Remote Similarity	NPC26029
0.6327	Remote Similarity	NPC307063
0.6327	Remote Similarity	NPC204233
0.6275	Remote Similarity	NPC267753
0.5918	Remote Similarity	NPC290791
0.5918	Remote Similarity	NPC292419
0.5636	Remote Similarity	NPC168511
0.549	Remote Similarity	NPC469987
0.5472	Remote Similarity	NPC225467
0.5357	Remote Similarity	NPC18955
0.5345	Remote Similarity	NPC68426
0.5273	Remote Similarity	NPC180777
0.5273	Remote Similarity	NPC103647
0.5179	Remote Similarity	NPC477229
0.5172	Remote Similarity	NPC282905

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC130011 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7198
0.1-0.2	1909
0.2-0.3	43
0.3-0.4	0
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