NPASS Compound

Natural Product: NPC37038

Natural Product ID	NPC37038
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Olean-12-En-4-Hydroxy-3,28-Dioic Acid
IUPAC Name	(1R,2R,4aR,4bS,6aS,10aS,12aR)-1-(2-carboxyethyl)-2-(2-hydroxypropan-2-yl)-1,4a,4b,9,9-pentamethyl-3,4,5,6,7,8,10,10a,12,12a-decahydro-2H-chrysene-6a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1631522
PubChem CID	53322486
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003364] Steroid acids [CHEMONTID:0003368] 3-carboxy steroids

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 86 0 0 0 0 0 0 0 0999 V2000 -2.6472 0.0753 4.5026 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9278 -0.0765 3.9927 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9341 -0.1003 4.7299 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1670 -0.2234 2.4878 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8685 -0.1701 1.8521 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7191 -0.3515 0.3471 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2586 -1.7460 0.0558 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4688 0.7003 -0.3597 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7636 1.3945 -1.4873 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3040 1.6340 -1.2560 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6006 0.2679 -1.0339 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2345 -0.2855 0.1497 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6762 -1.6371 0.4911 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7787 -1.4692 0.5512 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5125 -0.5178 0.0232 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8643 0.5700 -0.7505 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0122 1.9104 -0.0588 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6256 0.7615 -2.0733 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1124 0.8529 -1.8184 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6305 -0.3570 -1.0893 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9714 -0.6271 0.2298 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5264 0.0083 1.4356 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0198 -0.2155 1.4729 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7582 1.1279 1.4568 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4729 -0.9306 2.7305 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5379 -0.9895 0.2952 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1400 -0.3236 -1.0144 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2963 -1.5128 -1.9716 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5606 -2.4624 -1.6148 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8175 -1.5534 -3.2531 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7887 -0.4466 -2.3359 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8158 0.3729 -0.9441 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8001 -0.6532 -1.8766 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1805 1.6095 -1.8378 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9975 0.2788 -0.0747 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4646 0.0421 5.5062 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7008 0.7643 2.2865 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8434 -1.0432 2.3827 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1817 -0.8534 2.4390 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4092 0.8428 2.1430 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3394 -1.7957 0.2602 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6824 -2.4712 0.6495 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1505 -2.0587 -0.9958 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6870 1.5261 0.3895 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9500 0.8088 -2.4175 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 2.3793 -1.6354 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2310 2.2781 -0.3839 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9518 2.0513 -2.2179 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8816 0.4077 0.9997 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0316 -2.0608 1.4568 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8814 -2.4023 -0.2809 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3193 -2.2549 1.1204 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4337 2.0062 0.8530 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0953 2.1920 0.0450 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6844 2.7487 -0.7385 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3498 1.7652 -2.4574 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4688 -0.0605 -2.7685 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5841 0.7891 -2.8471 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4498 1.8076 -1.4204 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2714 -1.7230 0.3935 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1220 -0.5742 2.3207 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3489 1.0359 1.6653 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7977 1.0089 1.0938 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8164 1.5731 2.4688 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2471 1.8627 0.8055 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4877 -0.2263 3.6056 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5212 -1.2774 2.5324 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8562 -1.8278 2.9530 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6590 -0.9048 0.3340 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2810 -2.0480 0.2879 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6242 -0.9191 -1.8169 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5260 0.6932 -1.0955 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8165 -2.3869 -3.8285 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6137 0.1981 -3.2216 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1100 -1.3128 -2.4663 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8038 -0.8490 -2.5049 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6580 -1.1394 -1.9123 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1929 2.5242 -1.2570 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2727 1.4183 -2.0919 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6835 1.5942 -2.7935 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2103 -0.6083 0.4901 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8932 0.3313 -0.7997 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1882 1.2334 0.5156 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 6 5 1 1 6 7 1 0 6 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 2 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 23 26 1 0 26 27 1 0 20 28 1 6 28 29 2 0 28 30 1 0 11 31 1 6 8 32 1 0 32 33 1 0 32 34 1 0 32 35 1 0 12 6 1 0 21 15 1 0 16 11 1 0 27 20 1 0 1 36 1 0 4 37 1 0 4 38 1 0 5 39 1 0 5 40 1 0 7 41 1 0 7 42 1 0 7 43 1 0 8 44 1 1 9 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 12 49 1 1 13 50 1 0 13 51 1 0 14 52 1 0 17 53 1 0 17 54 1 0 17 55 1 0 18 56 1 0 18 57 1 0 19 58 1 0 19 59 1 0 21 60 1 1 22 61 1 0 22 62 1 0 24 63 1 0 24 64 1 0 24 65 1 0 25 66 1 0 25 67 1 0 25 68 1 0 26 69 1 0 26 70 1 0 27 71 1 0 27 72 1 0 30 73 1 0 31 74 1 0 31 75 1 0 31 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	HBMBVLYBFSJKDN-FUAOEXFOSA-N
Standard InCHI	InChI=1S/C30H48O5/c1-25(2)14-16-30(24(33)34)17-15-28(6)19(20(30)18-25)8-9-22-27(5,12-11-23(31)32)21(26(3,4)35)10-13-29(22,28)7/h8,20-22,35H,9-18H2,1-7H3,(H,31,32)(H,33,34)/t20-,21-,22+,27-,28+,29+,30-/m0/s1
SMILES	OC(=O)CC[C@@]1(C)[C@@H](CC[C@@]2([C@@H]1CC=C1[C@@]2(C)CC[C@@]2([C@H]1CC(C)(C)CC2)C(=O)O)C)C(O)(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.35	Volume:	529.252 ? Van der Waals volume.
Dense:	0.923	LogP:	3.804 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.091 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.399 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	23.0
TPSA:	94.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.375	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.722	Fsp³:	0.867
MCE-18:	92.571 ? 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:	0.735	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? 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:	0.473	Promiscuous compounds:	0.064

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.251	MDCK Permeability:	-4.983
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
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%):	0.0	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.121	MRP1:	0.98
Plasma Protein Binding (PPB):	96.137%	Volume Distribution (VD):	-0.564
Fu:	4.547% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.906	BCRP inhibitor:	0.001
BSEP inhibitor:	0.957

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.861	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.716	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.333
HLM stability:	0.182 ? 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):

1.706

Half-life (T1/2):

1.268

ADMET: Toxicity

hERG Blockers:	0.015	hERG Blockers (10um):	0.018
Human Hepatotoxicity (H-HT):	0.682	Drug-induced Liver Injury (DILI):	0.409
AMES Toxicity:	0.092	Rat Oral Acute Toxicity:	0.343
Maximum Recommended Daily Dose:	0.365	Skin Sensitization:	0.552
Carcinogencity:	0.777	Eye Corrosion:	0.008
Eye Irritation:	0.511	Respiratory Toxicity:	0.904
Drug-induced Neurotoxicity:	0.068	Ototoxicity:	0.828
Hematotoxicity:	0.607	Drug-induced Nephrotoxicity:	0.916
Genotoxicity:	0.731	RPMI-8226 Immunitoxicity:	0.028
A549 Cytotoxicity:	0.005	Hek293 Cytotoxicity:	0.021
BCF:	0.6 ? 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:	3.549 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.207 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.201 ? 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
NPO7123	Aria intermedia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7123	Aria intermedia	Species	Rosaceae	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
Inhibition	1

Activity Type	# Activity
Individual protein	1

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	Inhibition	=	-4.12	%	PMID[20964318]

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 NPC37038 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	24850
0.1-0.2	21892
0.2-0.3	2525
0.3-0.4	318
0.4-0.5	199
0.5-0.6	39
0.6-0.7	21
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
0.7869	Intermediate Similarity	NPC280654
0.7231	Intermediate Similarity	NPC275809
0.7121	Intermediate Similarity	NPC481360
0.6769	Remote Similarity	NPC231431
0.6567	Remote Similarity	NPC480946
0.6567	Remote Similarity	NPC130577
0.6567	Remote Similarity	NPC142415
0.6567	Remote Similarity	NPC102683
0.6471	Remote Similarity	NPC270768
0.6471	Remote Similarity	NPC59263
0.6471	Remote Similarity	NPC210106
0.6471	Remote Similarity	NPC282616
0.6471	Remote Similarity	NPC84319
0.6471	Remote Similarity	NPC52021
0.6471	Remote Similarity	NPC599947
0.6462	Remote Similarity	NPC604575
0.6377	Remote Similarity	NPC106112
0.6377	Remote Similarity	NPC261935
0.6377	Remote Similarity	NPC231063
0.6377	Remote Similarity	NPC282395
0.6377	Remote Similarity	NPC158141
0.6377	Remote Similarity	NPC110308
0.6286	Remote Similarity	NPC298554
0.6	Remote Similarity	NPC156981
0.5833	Remote Similarity	NPC200752
0.5833	Remote Similarity	NPC120840
0.5811	Remote Similarity	NPC324063
0.5775	Remote Similarity	NPC307282
0.5775	Remote Similarity	NPC64872
0.5775	Remote Similarity	NPC25906
0.5753	Remote Similarity	NPC474963
0.5694	Remote Similarity	NPC130278
0.5616	Remote Similarity	NPC291028
0.56	Remote Similarity	NPC296164
0.56	Remote Similarity	NPC480941
0.5556	Remote Similarity	NPC204407
0.5556	Remote Similarity	NPC182797
0.5556	Remote Similarity	NPC121798
0.5556	Remote Similarity	NPC234346
0.5556	Remote Similarity	NPC52169
0.5556	Remote Similarity	NPC488562
0.5526	Remote Similarity	NPC96580
0.5488	Remote Similarity	NPC606107
0.5479	Remote Similarity	NPC472149
0.5479	Remote Similarity	NPC609452
0.5455	Remote Similarity	NPC474727
0.5417	Remote Similarity	NPC474806
0.5417	Remote Similarity	NPC198664
0.5417	Remote Similarity	NPC133579
0.5342	Remote Similarity	NPC32118
0.5316	Remote Similarity	NPC481362
0.5301	Remote Similarity	NPC283849
0.5301	Remote Similarity	NPC28198
0.5301	Remote Similarity	NPC476123
0.527	Remote Similarity	NPC271614
0.527	Remote Similarity	NPC88116
0.5176	Remote Similarity	NPC286347
0.5143	Remote Similarity	NPC471899
0.5132	Remote Similarity	NPC201657
0.5125	Remote Similarity	NPC188833
0.5116	Remote Similarity	NPC100383
0.5067	Remote Similarity	NPC481314
0.5065	Remote Similarity	NPC130520

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC37038 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6576
0.1-0.2	2512
0.2-0.3	58
0.3-0.4	4
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