NPASS Compound

Natural Product: NPC183587

Natural Product ID	NPC183587
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OOQRHGBPHULERW-DPGDLXMDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44575258
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene glycosides

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 91 95 0 0 0 0 0 0 0 0999 V2000 -4.3886 -2.8729 1.5647 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0118 -2.2466 0.4870 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2503 -3.0472 -0.5432 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0131 -2.2979 -0.9652 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1515 -0.8222 -1.0424 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9083 -0.0985 -1.4972 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1387 0.5316 -2.8929 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6014 1.0468 -0.5885 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7961 1.9901 -0.3784 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0107 1.2577 0.0443 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8217 -0.2357 0.1774 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1746 -0.5924 1.4747 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2361 -0.8148 0.1880 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1330 -0.0411 1.0283 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5660 -0.4844 1.0661 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3006 0.4504 1.9755 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3192 1.2405 1.7139 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7088 1.9828 2.9383 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8285 1.5539 3.9397 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9581 0.6189 3.3785 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0367 0.0499 4.0598 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2537 -1.0078 -1.7000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4388 -0.5758 -2.1213 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3092 0.2172 -1.4965 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7134 -0.4098 -1.3999 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6895 0.2021 -2.3762 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7180 1.7130 -2.2550 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3961 2.1735 -1.6196 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1801 3.6432 -1.8470 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2754 3.8626 -3.2289 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4631 1.3701 -2.2694 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7416 2.2082 -1.4840 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4185 -0.1122 -3.7038 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1920 -0.4553 -0.1181 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3361 -1.6857 0.4672 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8466 -1.8691 0.7145 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0798 -1.2160 2.0658 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7334 0.1371 1.9247 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7272 0.7229 3.2061 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6784 -1.0116 2.5685 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8539 -1.7763 1.7453 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7450 -2.0513 2.9511 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0673 -3.2450 0.8929 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1539 -3.9472 1.7032 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9155 -2.4469 2.3947 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9548 -3.2054 -1.3759 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0222 -4.0190 -0.0980 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2028 -2.6631 -0.3028 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7950 -2.6763 -2.0045 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9167 -0.6485 -1.8692 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5707 -0.2799 -3.5222 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1589 0.7890 -3.3474 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7397 1.4357 -2.8508 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1438 1.7617 -1.0558 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1566 0.7714 0.3851 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9124 2.6354 -1.2566 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4150 2.6968 0.4288 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8019 1.4796 -0.7349 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3096 1.6414 1.0398 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3715 -1.3457 1.3773 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8995 -1.0409 2.2179 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8290 0.3352 2.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6508 -0.7268 -0.8886 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8056 0.1119 2.0812 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1828 1.0099 0.6149 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9767 -0.3932 0.0162 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7580 -1.4855 1.4754 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7882 1.3232 0.7465 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5732 3.0932 2.8044 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7707 1.8263 3.2229 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0141 -1.8722 -2.3846 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3907 -1.5591 -0.6913 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9722 0.5181 -0.4933 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5564 -1.4555 -1.7175 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7016 -0.1673 -2.1512 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7536 2.2003 -3.2413 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3958 1.9909 -0.5283 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9156 4.2106 -1.2683 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1717 3.9621 -1.5284 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3522 4.8423 -3.3356 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5339 2.2512 -0.5138 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8030 0.6345 -4.2676 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0368 -2.5524 -0.1163 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4469 -1.4599 -0.0942 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7936 0.0682 1.6251 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1041 0.7661 1.2960 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5873 1.1842 3.3859 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5471 -1.4095 3.6028 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3267 0.0361 2.4996 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0446 -2.6127 3.4091 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5649 -3.6114 1.6355 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 1 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 6 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 27 32 1 0 26 33 1 0 25 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 37 40 1 0 40 41 1 0 37 42 1 1 36 43 1 0 13 2 1 0 20 16 1 0 31 24 1 0 41 35 1 0 11 5 1 0 1 44 1 0 1 45 1 0 3 46 1 0 3 47 1 0 4 48 1 0 4 49 1 0 5 50 1 6 7 51 1 0 7 52 1 0 7 53 1 0 8 54 1 0 8 55 1 0 9 56 1 0 9 57 1 0 10 58 1 0 10 59 1 0 12 60 1 0 12 61 1 0 12 62 1 0 13 63 1 6 14 64 1 0 14 65 1 0 15 66 1 0 15 67 1 0 17 68 1 0 18 69 1 0 18 70 1 0 22 71 1 0 22 72 1 0 24 73 1 1 25 74 1 6 26 75 1 1 27 76 1 6 28 77 1 1 29 78 1 0 29 79 1 0 30 80 1 0 32 81 1 0 33 82 1 0 35 83 1 6 36 84 1 6 38 85 1 0 38 86 1 0 39 87 1 0 40 88 1 0 40 89 1 0 42 90 1 0 43 91 1 0 M END

Standard InCHIKey	OOQRHGBPHULERW-DPGDLXMDSA-N
Standard InCHI	InChI=1S/C31H48O12/c1-17-5-8-21-29(2,10-4-11-30(21,3)19(17)7-6-18-9-12-39-26(18)37)15-40-27-24(23(35)22(34)20(13-32)42-27)43-28-25(36)31(38,14-33)16-41-28/h9,19-25,27-28,32-36,38H,1,4-8,10-16H2,2-3H3/t19-,20-,21-,22-,23+,24-,25+,27-,28+,29+,30+,31-/m1/s1
SMILES	C=C1CC[C@@H]2[C@@](C)(CCC[C@@]2(C)[C@@H]1CCC1=CCOC1=O)CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@@](CO)(CO1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	612.31	Volume:	599.523 ? Van der Waals volume.
Dense:	1.021	LogP:	1.664 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.311 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.478 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	29.0
TPSA:	184.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.147	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.559	Fsp³:	0.839
MCE-18:	96.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.567	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.14	Promiscuous compounds:	0.24

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.976	MDCK Permeability:	-5.117
Pgp-inhibitor:	0.001	Pgp-substrate:	0.001
PAMPA:	0.691 ? 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):	0.057
20% Bioavailability (F20%):	0.129	30% Bioavailability (F30%):	0.989
50% Bioavailability (F50%):	0.932

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.355	MRP1:	0.376
Plasma Protein Binding (PPB):	82.017%	Volume Distribution (VD):	-0.517
Fu:	14.58% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.008
BSEP inhibitor:	0.15

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.631	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.018	CYP3A4-substrate:	0.589
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.065
HLM stability:	0.136 ? 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):

1.32

Half-life (T1/2):

1.672

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.029
Human Hepatotoxicity (H-HT):	0.852	Drug-induced Liver Injury (DILI):	0.495
AMES Toxicity:	0.93	Rat Oral Acute Toxicity:	0.088
Maximum Recommended Daily Dose:	0.165	Skin Sensitization:	1.0
Carcinogencity:	0.879	Eye Corrosion:	0.0
Eye Irritation:	0.023	Respiratory Toxicity:	0.056
Drug-induced Neurotoxicity:	0.078	Ototoxicity:	0.969
Hematotoxicity:	0.681	Drug-induced Nephrotoxicity:	0.964
Genotoxicity:	0.836	RPMI-8226 Immunitoxicity:	0.246
A549 Cytotoxicity:	0.81	Hek293 Cytotoxicity:	0.71
BCF:	1.069 ? 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:	3.848 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.684 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.704 ? 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
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1111/ppl.12252]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15894448]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	root	n.a.	PMID[15894448]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	aerial parts	purchased in Juhuacun herbal market, Kunming, Yunnan Province, China	2002-Oct	PMID[16562826]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18357994]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21598983]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22026410]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377022]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3578	Andrographis paniculata	Species	Acanthaceae	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 NPC183587 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	18657
0.1-0.2	25622
0.2-0.3	5254
0.3-0.4	290
0.4-0.5	24
0.5-0.6	9
0.6-0.7	3
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
0.6962	Remote Similarity	NPC392
0.6962	Remote Similarity	NPC177524
0.6962	Remote Similarity	NPC219900
0.5714	Remote Similarity	NPC479457
0.5698	Remote Similarity	NPC479461
0.5465	Remote Similarity	NPC599990
0.5263	Remote Similarity	NPC106416
0.5263	Remote Similarity	NPC86316
0.5263	Remote Similarity	NPC609165
0.5169	Remote Similarity	NPC479455
0.5169	Remote Similarity	NPC479454
0.5111	Remote Similarity	NPC479460

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC183587 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6812
0.1-0.2	2272
0.2-0.3	62
0.3-0.4	2
0.4-0.5	1
0.5-0.6	0
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
0.6962	Remote Similarity	NPD6686	Approved

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