NPASS Compound

Natural Product: NPC477872

Natural Product ID	NPC477872
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2R,4S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bR)-4,10-dihydroxy-2,6a,6b,9,9,12a-hexamethyl-3,4,4a,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-2-carboxylic acid
IUPAC Name	(2R,4S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bR)-4,10-dihydroxy-2,6a,6b,9,9,12a-hexamethyl-3,4,4a,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44577081
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 79 83 0 0 0 0 0 0 0 0999 V2000 -2.9055 1.4318 1.3264 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5612 0.7659 0.0632 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9200 1.7375 -1.0775 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3567 2.0460 -1.1456 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3069 0.9994 -0.6951 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7604 -0.3577 -0.4833 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3070 -0.4891 -0.2792 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9039 -1.5884 0.6782 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4632 -1.9745 0.3275 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5967 -0.7573 0.5275 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0926 0.4525 -0.1606 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1871 1.6133 -0.0921 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1727 1.2675 0.3716 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7166 0.0806 0.4295 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8056 -1.0285 -0.0477 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3305 -2.3321 0.4042 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7584 -2.5968 0.0019 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7025 -1.4616 0.2997 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0455 -0.2883 0.9352 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0001 0.7963 1.2241 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0981 1.0375 0.2174 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7120 -0.2189 -0.2950 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6683 -1.1882 -0.7992 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1867 -0.8667 -2.0219 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6765 1.8989 -0.9475 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1548 1.8027 0.9285 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2993 1.3080 1.0191 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9338 3.0367 1.4956 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7988 -0.9405 -1.5329 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4411 -0.6078 2.0240 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1702 -1.2434 -1.6773 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5058 -0.9778 0.7087 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0570 1.4257 0.4347 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5751 2.3334 1.1629 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0296 1.9110 1.8524 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4318 0.8411 2.0847 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3466 2.6875 -0.9585 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5877 1.2805 -2.0236 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5656 2.4186 -2.1950 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5418 2.9679 -0.5164 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1208 0.9571 -1.4860 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8496 -0.8086 -1.2693 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9090 -1.2999 1.7263 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4985 -2.5177 0.4883 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4818 -2.3562 -0.6881 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0847 -2.7752 0.9918 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0980 0.1576 -1.2680 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5441 2.4376 0.5701 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0478 2.1099 -1.0941 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7935 2.0984 0.7002 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3288 -2.4152 1.5292 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7182 -3.1510 0.0281 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8865 -2.9236 -1.0494 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0352 -3.5332 0.5810 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3850 -1.8742 1.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7623 -0.6994 1.9824 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5864 0.4941 2.1553 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6008 1.7695 1.5012 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3513 0.0427 -1.1658 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2782 -0.7329 0.4987 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2426 -2.1583 -0.9358 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5214 -0.1714 -2.1032 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0036 2.9707 -0.8007 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5765 1.9747 -1.0585 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1189 1.5999 -1.9058 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6789 3.6384 1.8527 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6216 -1.6222 -1.9058 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0576 0.0533 -1.9507 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1048 -1.3740 -2.0119 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -0.2671 2.5293 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2882 -1.6333 2.4837 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3452 0.0903 2.3367 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2649 -1.3973 -1.6976 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8014 -0.7353 -2.6042 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6530 -2.1927 -1.5488 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8193 -2.0159 0.5126 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9183 -0.9777 1.6232 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4389 -0.4066 0.9170 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0507 2.4220 0.4449 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 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 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 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 21 25 1 6 21 26 1 0 26 27 2 0 26 28 1 0 15 29 1 6 10 30 1 1 6 31 1 0 6 32 1 0 5 33 1 0 7 2 1 0 11 2 1 0 15 10 1 0 19 14 1 0 23 18 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 5 41 1 6 7 42 1 6 8 43 1 0 8 44 1 0 9 45 1 0 9 46 1 0 11 47 1 6 12 48 1 0 12 49 1 0 13 50 1 0 16 51 1 0 16 52 1 0 17 53 1 0 17 54 1 0 18 55 1 1 19 56 1 1 20 57 1 0 20 58 1 0 22 59 1 0 22 60 1 0 23 61 1 6 24 62 1 0 25 63 1 0 25 64 1 0 25 65 1 0 28 66 1 0 29 67 1 0 29 68 1 0 29 69 1 0 30 70 1 0 30 71 1 0 30 72 1 0 31 73 1 0 31 74 1 0 31 75 1 0 32 76 1 0 32 77 1 0 32 78 1 0 33 79 1 0 M END

Standard InCHIKey	OOFHJOXAWBEIEP-XSWDGSHTSA-N
Standard InCHI	InChI=1S/C29H46O4/c1-25(2)21-10-14-29(6)22(27(21,4)12-11-23(25)31)8-7-19-18-15-26(3,24(32)33)16-20(30)17(18)9-13-28(19,29)5/h7,17-18,20-23,30-31H,8-16H2,1-6H3,(H,32,33)/t17-,18-,20+,21+,22-,23+,26-,27+,28-,29-/m1/s1
SMILES	C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@H]5[C@H]4C[C@@](C[C@@H]5O)(C)C(=O)O)C)C)(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	458.34	Volume:	497.246 ? Van der Waals volume.
Dense:	0.922	LogP:	3.144 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.03 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.516 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.433	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.975	Fsp³:	0.897
MCE-18:	103.636 ? 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:	0.803	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.022 ? 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:	0.36	Promiscuous compounds:	0.069

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.456	MDCK Permeability:	-4.982
Pgp-inhibitor:	0.0	Pgp-substrate:	0.226
PAMPA:	0.998 ? 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%):	0.363	30% Bioavailability (F30%):	0.019
50% Bioavailability (F50%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022	MRP1:	0.946
Plasma Protein Binding (PPB):	82.075%	Volume Distribution (VD):	-0.274
Fu:	14.974% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.99
OATP1B3 inhibitor:	0.003	BCRP inhibitor:	0.276
BSEP inhibitor:	0.618

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.004 ? 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):

3.615

Half-life (T1/2):

1.904

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.036
Human Hepatotoxicity (H-HT):	0.523	Drug-induced Liver Injury (DILI):	0.239
AMES Toxicity:	0.174	Rat Oral Acute Toxicity:	0.276
Maximum Recommended Daily Dose:	0.525	Skin Sensitization:	0.985
Carcinogencity:	0.864	Eye Corrosion:	0.024
Eye Irritation:	0.47	Respiratory Toxicity:	0.833
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.572
Hematotoxicity:	0.603	Drug-induced Nephrotoxicity:	0.86
Genotoxicity:	0.539	RPMI-8226 Immunitoxicity:	0.059
A549 Cytotoxicity:	0.188	Hek293 Cytotoxicity:	0.215
BCF:	1.007 ? 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:	3.652 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.304 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.544 ? 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
NPO8737	Saussurea muliensis	Species	Asteraceae	Eukaryota	flowers and roots	Muli Autonomous County of Sichuan, China	2005-AUG	PMID[18419156]
NPO8737	Saussurea muliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8737	Saussurea muliensis	Species	Asteraceae	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
MIC	4

Activity Type	# Activity
Organism	4

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
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	50	ug/ml	PMID[18419156]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	50	ug/ml	PMID[18419156]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50	ug/ml	PMID[18419156]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	>	50	ug/ml	PMID[18419156]

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 NPC477872 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	22503
0.1-0.2	22577
0.2-0.3	3582
0.3-0.4	862
0.4-0.5	246
0.5-0.6	58
0.6-0.7	24
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
0.746	Intermediate Similarity	NPC7260
0.746	Intermediate Similarity	NPC210037
0.746	Intermediate Similarity	NPC120968
0.746	Intermediate Similarity	NPC227467
0.746	Intermediate Similarity	NPC273621
0.6923	Remote Similarity	NPC171203
0.6923	Remote Similarity	NPC307426
0.6923	Remote Similarity	NPC98442
0.6923	Remote Similarity	NPC242468
0.6923	Remote Similarity	NPC112866
0.6515	Remote Similarity	NPC480946
0.6515	Remote Similarity	NPC187722
0.6515	Remote Similarity	NPC130577
0.6515	Remote Similarity	NPC142415
0.6515	Remote Similarity	NPC102683
0.6418	Remote Similarity	NPC182797
0.6418	Remote Similarity	NPC51700
0.6418	Remote Similarity	NPC88716
0.6418	Remote Similarity	NPC68160
0.6418	Remote Similarity	NPC52169
0.6418	Remote Similarity	NPC488562
0.6418	Remote Similarity	NPC606443
0.6232	Remote Similarity	NPC202728
0.6232	Remote Similarity	NPC158059
0.6232	Remote Similarity	NPC293564
0.6029	Remote Similarity	NPC610937
0.6	Remote Similarity	NPC228784
0.6	Remote Similarity	NPC324341
0.6	Remote Similarity	NPC601810
0.5915	Remote Similarity	NPC263393
0.5857	Remote Similarity	NPC18872
0.5857	Remote Similarity	NPC290614
0.5797	Remote Similarity	NPC274330
0.5797	Remote Similarity	NPC198664
0.5714	Remote Similarity	NPC195019
0.5625	Remote Similarity	NPC290598
0.5625	Remote Similarity	NPC27765
0.5625	Remote Similarity	NPC120098
0.5625	Remote Similarity	NPC30590
0.5625	Remote Similarity	NPC122418
0.5625	Remote Similarity	NPC491014
0.5556	Remote Similarity	NPC29765
0.5522	Remote Similarity	NPC235341
0.5513	Remote Similarity	NPC603645
0.5493	Remote Similarity	NPC270768
0.5493	Remote Similarity	NPC59263
0.5493	Remote Similarity	NPC210106
0.5493	Remote Similarity	NPC229281
0.5493	Remote Similarity	NPC121798
0.5493	Remote Similarity	NPC234346
0.5479	Remote Similarity	NPC193750
0.5417	Remote Similarity	NPC61543
0.5417	Remote Similarity	NPC293048
0.5417	Remote Similarity	NPC225585
0.5373	Remote Similarity	NPC101475
0.5342	Remote Similarity	NPC155120
0.5342	Remote Similarity	NPC136697
0.5342	Remote Similarity	NPC288833
0.5342	Remote Similarity	NPC298554
0.5286	Remote Similarity	NPC246708
0.527	Remote Similarity	NPC191412
0.527	Remote Similarity	NPC114159
0.527	Remote Similarity	NPC6818
0.5217	Remote Similarity	NPC95594
0.5211	Remote Similarity	NPC477579
0.5205	Remote Similarity	NPC472240
0.5205	Remote Similarity	NPC262858
0.52	Remote Similarity	NPC127689
0.52	Remote Similarity	NPC130520
0.5147	Remote Similarity	NPC311078
0.5147	Remote Similarity	NPC34177
0.5139	Remote Similarity	NPC86372
0.5132	Remote Similarity	NPC187933
0.5132	Remote Similarity	NPC116457
0.5072	Remote Similarity	NPC253807
0.5072	Remote Similarity	NPC40394
0.5072	Remote Similarity	NPC158662
0.5072	Remote Similarity	NPC291379
0.507	Remote Similarity	NPC40552
0.5068	Remote Similarity	NPC142361
0.5068	Remote Similarity	NPC474684
0.5067	Remote Similarity	NPC4036
0.5067	Remote Similarity	NPC65120
0.5067	Remote Similarity	NPC145067
0.5067	Remote Similarity	NPC233455
0.5067	Remote Similarity	NPC158030
0.5067	Remote Similarity	NPC474525

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6390
0.1-0.2	2690
0.2-0.3	62
0.3-0.4	5
0.4-0.5	2
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
0.5067	Remote Similarity	NPD7515	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