NPASS Compound

Natural Product: NPC191412

Natural Product ID	NPC191412
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Barbinervic Acid
IUPAC Name	(1R,2R,4aS,6aR,6aS,6bR,8aR,9S,10R,12aR,14bS)-1,10-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms	Barbinervic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL523209
PubChem CID	194183
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 83 87 0 0 0 0 0 0 0 0999 V2000 -6.9557 0.8459 0.2159 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5815 1.0648 0.3172 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8469 -0.2482 0.3503 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3985 -0.9688 1.5946 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2951 -1.0612 -0.8290 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5576 -1.6187 -0.5035 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3939 -2.1894 -1.1570 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9445 -1.9587 -1.0621 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5863 -0.4847 -0.7745 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3755 -0.1420 0.4613 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8723 1.1041 1.1488 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4575 0.8190 1.6296 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 0.6425 0.3509 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1313 -0.5541 -0.3403 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2486 -1.1270 -1.4036 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1628 -0.7423 -1.2887 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7046 -0.0445 -0.2894 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8030 0.3837 0.8065 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8626 -0.5237 1.9978 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3649 1.7364 1.2771 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8223 1.5058 1.6885 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6146 1.4263 0.4078 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1474 0.2332 -0.3739 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0554 -0.9086 -0.0637 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5467 -2.2630 -0.4081 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4423 -0.9547 1.2952 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3769 -0.6022 -0.7889 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9229 0.6798 -0.2834 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0752 1.4235 0.6893 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3406 -1.7529 -0.7007 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2756 2.6484 -0.4058 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7778 2.5901 -1.5461 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5477 3.8649 0.1825 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6627 1.9408 -0.3481 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8647 0.2602 -2.0054 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1951 0.8166 -0.7562 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3005 1.7498 -0.4743 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4476 1.6331 1.2861 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4932 -1.0642 1.4152 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8913 -1.9398 1.7071 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2401 -0.3005 2.4604 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5326 -0.3885 -1.7050 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7946 -2.1715 -1.3053 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6330 -2.5260 -2.2035 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6919 -3.0715 -0.5186 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4080 -2.2202 -2.0065 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4967 -2.6152 -0.2808 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0566 -0.9646 1.1822 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9956 2.0254 0.6064 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4860 1.1953 2.0923 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1437 1.7120 2.1986 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5121 -0.0856 2.2322 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1647 -1.3636 0.4618 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5699 -0.8788 -2.4464 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2620 -2.2597 -1.3971 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8060 -1.0771 -2.1239 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8330 -1.0507 2.0914 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7624 0.0604 2.9599 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1002 -1.3036 2.0454 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4326 2.4553 0.4211 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8499 2.1251 2.1523 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1288 2.4328 2.2544 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9350 0.6445 2.3408 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3419 0.4980 -1.4598 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6624 -2.4500 -1.4886 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5176 -2.3858 -0.0702 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1390 -3.0184 0.1899 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3616 -1.2532 1.4092 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0960 -0.4739 -1.8592 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2335 1.3513 -1.1366 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8989 0.4494 0.2363 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2945 1.1578 1.7668 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4246 2.5012 0.6439 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8723 -2.7255 -0.8369 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0754 -1.6428 -1.5514 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9556 -1.6940 0.2153 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4172 4.7148 -0.3346 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5707 2.7474 0.4440 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1378 2.0050 -1.1042 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5992 2.2043 -0.8594 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4041 -0.3498 -2.7975 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4829 1.1718 -1.9129 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9518 0.5985 -2.5837 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 6 3 4 1 0 3 5 1 0 5 6 1 0 5 7 1 0 7 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 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 1 24 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 22 31 1 6 31 32 2 0 31 33 1 0 13 34 1 6 9 35 1 6 10 3 1 0 18 13 1 0 29 22 1 0 14 9 1 0 23 17 1 0 1 36 1 0 2 37 1 0 2 38 1 0 4 39 1 0 4 40 1 0 4 41 1 0 5 42 1 6 6 43 1 0 7 44 1 0 7 45 1 0 8 46 1 0 8 47 1 0 10 48 1 1 11 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 14 53 1 1 15 54 1 0 15 55 1 0 16 56 1 0 19 57 1 0 19 58 1 0 19 59 1 0 20 60 1 0 20 61 1 0 21 62 1 0 21 63 1 0 23 64 1 6 25 65 1 0 25 66 1 0 25 67 1 0 26 68 1 0 27 69 1 6 28 70 1 0 28 71 1 0 29 72 1 0 29 73 1 0 30 74 1 0 30 75 1 0 30 76 1 0 33 77 1 0 34 78 1 0 34 79 1 0 34 80 1 0 35 81 1 0 35 82 1 0 35 83 1 0 M END

Standard InCHIKey	YLHQFGOOMKJFLP-JGLQYCRZSA-N
Standard InCHI	InChI=1S/C30H48O5/c1-18-9-14-30(24(33)34)16-15-27(4)19(23(30)29(18,6)35)7-8-21-25(2)12-11-22(32)26(3,17-31)20(25)10-13-28(21,27)5/h7,18,20-23,31-32,35H,8-17H2,1-6H3,(H,33,34)/t18-,20-,21-,22-,23-,25+,26-,27-,28-,29-,30+/m1/s1
SMILES	OC[C@@]1(C)[C@H](O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@](C)(O)[C@@H](CC1)C)C(=O)O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.35	Volume:	523.332 ? Van der Waals volume.
Dense:	0.933	LogP:	2.848 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.661 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.419 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	97.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.402	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.008	Fsp³:	0.9
MCE-18:	108.07 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.471	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.067 ? 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:	0.319	Promiscuous compounds:	0.083

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.564	MDCK Permeability:	-5.115
Pgp-inhibitor:	0.003	Pgp-substrate:	0.041
PAMPA:	1.0 ? 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%):	0.697	30% Bioavailability (F30%):	0.098
50% Bioavailability (F50%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.314	MRP1:	0.998
Plasma Protein Binding (PPB):	76.635%	Volume Distribution (VD):	-0.431
Fu:	19.422% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.694	BCRP inhibitor:	0.007
BSEP inhibitor:	0.973

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.019	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.876	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.879	CYP3A4-substrate:	0.016
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.059
HLM stability:	0.003 ? 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):

4.777

Half-life (T1/2):

1.429

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.028
Human Hepatotoxicity (H-HT):	0.617	Drug-induced Liver Injury (DILI):	0.205
AMES Toxicity:	0.224	Rat Oral Acute Toxicity:	0.335
Maximum Recommended Daily Dose:	0.584	Skin Sensitization:	0.981
Carcinogencity:	0.977	Eye Corrosion:	0.004
Eye Irritation:	0.615	Respiratory Toxicity:	0.931
Drug-induced Neurotoxicity:	0.026	Ototoxicity:	0.626
Hematotoxicity:	0.217	Drug-induced Nephrotoxicity:	0.941
Genotoxicity:	0.867	RPMI-8226 Immunitoxicity:	0.054
A549 Cytotoxicity:	0.228	Hek293 Cytotoxicity:	0.304
BCF:	0.565 ? 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:	3.372 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.003 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.19 ? 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
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18798681]
NPO26817	Lysionotus pauciflorus	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775221]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[3430165]
NPO14438	Coussarea brevicaulis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26817	Lysionotus pauciflorus	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26817	Lysionotus pauciflorus	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14438	Coussarea brevicaulis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26817	Lysionotus pauciflorus	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26817	Lysionotus pauciflorus	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14438	Coussarea brevicaulis	Species	Rubiaceae	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
Inhibition	1

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	30000.0	nM	PMID[18798681]
NPT5212	Individual protein	Sentrin-specific protease 1	Homo sapiens	Inhibition	=	19.9	%	PMID[35500202]

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 NPC191412 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	23001
0.1-0.2	22579
0.2-0.3	3372
0.3-0.4	573
0.4-0.5	211
0.5-0.6	65
0.6-0.7	26
0.7-0.8	0
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC114159
1.0	High Similarity	NPC6818
0.8871	High Similarity	NPC136697
0.8571	High Similarity	NPC202728
0.8571	High Similarity	NPC158059
0.8182	Intermediate Similarity	NPC187933
0.803	Intermediate Similarity	NPC137072
0.7879	Intermediate Similarity	NPC247139
0.7647	Intermediate Similarity	NPC116457
0.7353	Intermediate Similarity	NPC118519
0.7353	Intermediate Similarity	NPC132824
0.7313	Intermediate Similarity	NPC61543
0.7313	Intermediate Similarity	NPC293048
0.7313	Intermediate Similarity	NPC225585
0.7246	Intermediate Similarity	NPC148964
0.7206	Intermediate Similarity	NPC259733
0.7206	Intermediate Similarity	NPC158371
0.7206	Intermediate Similarity	NPC207922
0.7164	Intermediate Similarity	NPC270768
0.7164	Intermediate Similarity	NPC59263
0.7164	Intermediate Similarity	NPC210106
0.7164	Intermediate Similarity	NPC229281
0.7164	Intermediate Similarity	NPC121798
0.7164	Intermediate Similarity	NPC234346
0.7	Intermediate Similarity	NPC62516
0.6901	Remote Similarity	NPC157113
0.6857	Remote Similarity	NPC35239
0.6812	Remote Similarity	NPC235053
0.6761	Remote Similarity	NPC127689
0.6761	Remote Similarity	NPC130520
0.6757	Remote Similarity	NPC96693
0.6714	Remote Similarity	NPC256247
0.6533	Remote Similarity	NPC54909
0.6533	Remote Similarity	NPC233012
0.6528	Remote Similarity	NPC118964
0.6486	Remote Similarity	NPC603658
0.6438	Remote Similarity	NPC284865
0.6389	Remote Similarity	NPC263393
0.6216	Remote Similarity	NPC147232
0.6197	Remote Similarity	NPC182797
0.6197	Remote Similarity	NPC51700
0.6197	Remote Similarity	NPC88716
0.6197	Remote Similarity	NPC68160
0.6197	Remote Similarity	NPC52169
0.6197	Remote Similarity	NPC488562
0.6056	Remote Similarity	NPC480946
0.6056	Remote Similarity	NPC187722
0.6056	Remote Similarity	NPC130577
0.6056	Remote Similarity	NPC142415
0.6056	Remote Similarity	NPC102683
0.6027	Remote Similarity	NPC293564
0.5946	Remote Similarity	NPC9613
0.5897	Remote Similarity	NPC327179
0.589	Remote Similarity	NPC88116
0.5875	Remote Similarity	NPC600756
0.5811	Remote Similarity	NPC32407
0.5811	Remote Similarity	NPC263548
0.5811	Remote Similarity	NPC298554
0.5811	Remote Similarity	NPC606320
0.5676	Remote Similarity	NPC231063
0.5676	Remote Similarity	NPC282395
0.5676	Remote Similarity	NPC73489
0.5676	Remote Similarity	NPC130278
0.5676	Remote Similarity	NPC173744
0.5676	Remote Similarity	NPC204961
0.5676	Remote Similarity	NPC73004
0.5676	Remote Similarity	NPC609452
0.5616	Remote Similarity	NPC274330
0.5584	Remote Similarity	NPC83693
0.5584	Remote Similarity	NPC174663
0.5556	Remote Similarity	NPC482052
0.5541	Remote Similarity	NPC606443
0.5493	Remote Similarity	NPC230295
0.5493	Remote Similarity	NPC98386
0.5467	Remote Similarity	NPC37221
0.5435	Remote Similarity	NPC482049
0.5435	Remote Similarity	NPC482050
0.5429	Remote Similarity	NPC196753
0.5405	Remote Similarity	NPC198664
0.5385	Remote Similarity	NPC20235
0.5385	Remote Similarity	NPC299996
0.5333	Remote Similarity	NPC275809
0.5333	Remote Similarity	NPC171203
0.5333	Remote Similarity	NPC307426
0.5333	Remote Similarity	NPC98442
0.5333	Remote Similarity	NPC242468
0.5326	Remote Similarity	NPC25491
0.5278	Remote Similarity	NPC253402
0.527	Remote Similarity	NPC477872
0.5263	Remote Similarity	NPC472149
0.5263	Remote Similarity	NPC71074
0.5263	Remote Similarity	NPC110308
0.5263	Remote Similarity	NPC605937
0.5213	Remote Similarity	NPC482051
0.52	Remote Similarity	NPC213412
0.5195	Remote Similarity	NPC173089
0.5195	Remote Similarity	NPC228784
0.5195	Remote Similarity	NPC324341
0.5195	Remote Similarity	NPC601810
0.5135	Remote Similarity	NPC488164
0.5135	Remote Similarity	NPC264005
0.5132	Remote Similarity	NPC7260
0.5132	Remote Similarity	NPC210037
0.5132	Remote Similarity	NPC282616
0.5132	Remote Similarity	NPC120968
0.5132	Remote Similarity	NPC64872
0.5132	Remote Similarity	NPC84319
0.5132	Remote Similarity	NPC25906
0.5132	Remote Similarity	NPC52021
0.5132	Remote Similarity	NPC227467
0.5132	Remote Similarity	NPC273621
0.5132	Remote Similarity	NPC599947
0.5125	Remote Similarity	NPC479743
0.5065	Remote Similarity	NPC38754
0.5065	Remote Similarity	NPC158141
0.5065	Remote Similarity	NPC481360

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC191412 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6669
0.1-0.2	2426
0.2-0.3	49
0.3-0.4	4
0.4-0.5	1
0.5-0.6	1
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
0.5132	Remote Similarity	NPD7645	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