NPASS Compound

Natural Product: NPC14112

Natural Product ID	NPC14112
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta,6Alpha-Dihydroxylup-20(29)-Ene
IUPAC Name	(1R,3aR,5aR,5bR,7S,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-7,9-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL525545
PubChem CID	10789350
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 -2.2807 -1.4954 4.4228 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1117 -1.0909 3.4903 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1215 -2.0298 2.9607 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0314 0.3031 2.9775 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4309 0.9089 3.0789 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9142 1.0909 1.6329 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6130 1.4447 0.9490 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1981 2.7909 1.4614 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6001 1.2740 -0.5146 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4246 0.6856 -1.1711 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3037 0.1496 -0.3533 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4177 -1.3442 -0.2892 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3646 0.6394 1.1025 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2876 0.1099 1.9563 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0540 0.6054 1.3949 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1380 0.1002 0.0031 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5195 0.1630 -0.6046 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0243 1.5425 -0.8316 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4546 -0.4428 0.4557 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8108 -0.7668 -0.1304 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6578 -1.6555 -1.3100 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7435 -1.1699 -2.3846 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4218 -2.4054 -3.2480 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4546 -0.2160 -3.2909 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4520 -0.6968 -1.8348 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5518 -0.0234 -2.8201 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1599 0.1388 -2.2919 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0487 0.6211 -0.8884 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0073 2.1381 -0.9252 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4730 -0.8795 -3.9454 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9358 -1.8835 -1.8541 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7484 0.3272 1.5298 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3328 -2.4975 4.7971 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5454 -0.8215 4.8162 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1478 -2.9872 3.5185 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1492 -1.6220 2.9773 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8952 -2.2997 1.9108 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3539 0.9210 3.5964 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1117 0.2943 3.6646 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3673 1.9247 3.5110 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6131 1.9334 1.5873 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2998 0.1417 1.2318 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6357 3.4134 0.7676 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7055 2.7000 2.4691 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1429 3.3721 1.6767 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8081 2.3018 -0.9504 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5636 0.7312 -0.7733 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0626 1.3801 -1.9944 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8073 -0.1677 -1.8210 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4980 -1.7489 0.7487 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6391 -1.9079 -0.7954 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3846 -1.6908 -0.7694 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2412 1.7639 1.1202 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2129 -0.9569 2.1055 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3707 0.5914 2.9496 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2182 1.6603 1.5601 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8143 0.0343 2.0058 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9481 -1.0156 0.0909 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6294 2.0729 -1.6893 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1382 1.4585 -1.0117 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9646 2.0921 0.1325 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0222 -1.3101 0.9486 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6495 0.3862 1.1994 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4592 0.1031 -0.2683 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3233 -1.3855 0.6660 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2581 -2.6391 -0.9334 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3933 -2.1606 -4.3150 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5016 -2.8891 -2.8633 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2347 -3.1770 -3.1366 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9711 -0.7758 -4.1281 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2825 0.3095 -2.7697 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7934 0.5063 -3.8078 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8944 -1.6297 -1.5090 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8962 0.9331 -3.2029 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3449 0.8899 -2.9716 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3855 -0.8100 -2.4892 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2934 2.5288 -1.9478 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0004 2.5553 -0.7455 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6524 2.6049 -0.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7442 -1.5245 -3.8390 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6319 -1.9087 -1.1664 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1545 -0.6112 1.0639 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 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 26 30 1 0 21 31 1 0 13 32 1 0 32 4 1 0 32 7 1 0 28 11 1 0 28 16 1 0 25 17 1 0 1 33 1 0 1 34 1 0 3 35 1 0 3 36 1 0 3 37 1 0 4 38 1 1 5 39 1 0 5 40 1 0 6 41 1 0 6 42 1 0 8 43 1 0 8 44 1 0 8 45 1 0 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 12 50 1 0 12 51 1 0 12 52 1 0 13 53 1 6 14 54 1 0 14 55 1 0 15 56 1 0 15 57 1 0 16 58 1 1 18 59 1 0 18 60 1 0 18 61 1 0 19 62 1 0 19 63 1 0 20 64 1 0 20 65 1 0 21 66 1 1 23 67 1 0 23 68 1 0 23 69 1 0 24 70 1 0 24 71 1 0 24 72 1 0 25 73 1 1 26 74 1 6 27 75 1 0 27 76 1 0 29 77 1 0 29 78 1 0 29 79 1 0 30 80 1 0 31 81 1 0 32 82 1 6 M END

Standard InCHIKey	DSXMIKAVZFWLFV-PAPKCNLDSA-N
Standard InCHI	InChI=1S/C30H50O2/c1-18(2)19-11-13-27(5)15-16-29(7)20(24(19)27)9-10-22-28(6)14-12-23(32)26(3,4)25(28)21(31)17-30(22,29)8/h19-25,31-32H,1,9-17H2,2-8H3/t19-,20+,21-,22+,23-,24+,25-,27+,28+,29+,30+/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@]2(C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5[C@H](C[C@@]34C)O)O)[C@@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	442.38	Volume:	499.598 ? Van der Waals volume.
Dense:	0.885	LogP:	5.022 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.373 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.325 ? 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:	0.429	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.883	Fsp³:	0.933
MCE-18:	103.517 ? 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:	0.949	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:	0.526	Promiscuous compounds:	0.271

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.212	MDCK Permeability:	-5.057
Pgp-inhibitor:	0.338	Pgp-substrate:	0.423
PAMPA:	0.063 ? 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%):	0.504	30% Bioavailability (F30%):	0.709
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988	MRP1:	0.988
Plasma Protein Binding (PPB):	96.052%	Volume Distribution (VD):	0.113
Fu:	4.165% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.655
BSEP inhibitor:	0.946

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.945	CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.064
CYP2D6-inhibitor:	0.036	CYP2D6-substrate:	0.627
CYP3A4-inhibitor:	0.806	CYP3A4-substrate:	0.905
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.025
HLM stability:	0.186 ? 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):

13.666

Half-life (T1/2):

0.523

ADMET: Toxicity

hERG Blockers:	0.097	hERG Blockers (10um):	0.274
Human Hepatotoxicity (H-HT):	0.593	Drug-induced Liver Injury (DILI):	0.299
AMES Toxicity:	0.292	Rat Oral Acute Toxicity:	0.254
Maximum Recommended Daily Dose:	0.534	Skin Sensitization:	0.955
Carcinogencity:	0.891	Eye Corrosion:	0.185
Eye Irritation:	0.848	Respiratory Toxicity:	0.793
Drug-induced Neurotoxicity:	0.071	Ototoxicity:	0.675
Hematotoxicity:	0.492	Drug-induced Nephrotoxicity:	0.669
Genotoxicity:	0.404	RPMI-8226 Immunitoxicity:	0.048
A549 Cytotoxicity:	0.29	Hek293 Cytotoxicity:	0.417
BCF:	2.327 ? 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:	4.122 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.149 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.832 ? 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
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1021/np100392m]
NPO32566	periploca aphylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869229]
NPO32566	periploca aphylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387640]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[20879743]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21190854]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21807513]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	stems and twigs	Beihai, Guangxi province, China	2008-Jan	PMID[22196120]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	bark	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	twig	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23501	Symphytum asperum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20429	Porophyllum riedelii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24294	Lolium cuneatum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21042	Penstemon richardsonii	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23501	Symphytum asperum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23501	Symphytum asperum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23415	Dalea tinctoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23060	Hedeoma pulegioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17883	Salvia infuscata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24294	Lolium cuneatum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23501	Symphytum asperum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20429	Porophyllum riedelii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21042	Penstemon richardsonii	Species	Plantaginaceae	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
IC50	1

Activity Type	# Activity
Others	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
NPT2	Others	Unspecified	n.a.	IC50	=	42500.0	nM	PMID[10869229]

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 NPC14112 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	29710
0.1-0.2	17703
0.2-0.3	2103
0.3-0.4	242
0.4-0.5	57
0.5-0.6	29
0.6-0.7	5
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	NPC86305
0.7451	Intermediate Similarity	NPC472741
0.7255	Intermediate Similarity	NPC192638
0.7255	Intermediate Similarity	NPC25511
0.7255	Intermediate Similarity	NPC600137
0.6364	Remote Similarity	NPC240235
0.625	Remote Similarity	NPC248830
0.625	Remote Similarity	NPC212241
0.6071	Remote Similarity	NPC202540
0.6034	Remote Similarity	NPC269396
0.5902	Remote Similarity	NPC472738
0.5902	Remote Similarity	NPC472739
0.5893	Remote Similarity	NPC102708
0.569	Remote Similarity	NPC231256
0.569	Remote Similarity	NPC178383
0.5636	Remote Similarity	NPC142712
0.5593	Remote Similarity	NPC93662
0.5536	Remote Similarity	NPC35652
0.5517	Remote Similarity	NPC104387
0.55	Remote Similarity	NPC246956
0.55	Remote Similarity	NPC74595
0.55	Remote Similarity	NPC264665
0.5484	Remote Similarity	NPC471900
0.5439	Remote Similarity	NPC80297
0.5439	Remote Similarity	NPC475727
0.5439	Remote Similarity	NPC116119
0.5323	Remote Similarity	NPC12774
0.5312	Remote Similarity	NPC607755
0.5263	Remote Similarity	NPC480925
0.5263	Remote Similarity	NPC48079
0.5254	Remote Similarity	NPC78067
0.5254	Remote Similarity	NPC144075
0.5254	Remote Similarity	NPC278091
0.5254	Remote Similarity	NPC301226
0.5238	Remote Similarity	NPC474482
0.5167	Remote Similarity	NPC300499
0.5085	Remote Similarity	NPC97534
0.5085	Remote Similarity	NPC195155
0.5079	Remote Similarity	NPC475745

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC14112 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7988
0.1-0.2	1115
0.2-0.3	45
0.3-0.4	0
0.4-0.5	2
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