NPASS Compound

Natural Product: NPC474727

Natural Product ID	NPC474727
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	25-Acetoxy-3R-Hydroxyolean-12-En-28-Oic Acid
IUPAC Name	(4aS,6aS,6aS,6bR,10R,12aS,14bS)-12a-(acetyloxymethyl)-10-hydroxy-2,2,6a,6b,9,9-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL480497
PubChem CID	11420932
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 87 91 0 0 0 0 0 0 0 0999 V2000 2.3728 1.0394 -4.9631 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7843 0.1618 -3.8504 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3517 -0.9512 -4.0967 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5932 0.4685 -2.5218 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9836 -0.3640 -1.4569 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6894 0.1458 -0.0966 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4085 1.4651 0.0792 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5136 1.4285 1.0858 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4486 0.2620 0.8941 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6339 -0.9852 1.0953 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9335 -1.4596 2.5317 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2140 -2.0430 0.1924 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1711 -0.7966 0.9930 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4547 -2.1217 0.8966 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0023 -1.8878 1.2056 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4027 -0.8340 0.3585 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0118 -1.4160 -0.9715 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2394 0.4058 0.2238 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5765 1.4821 -0.5319 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8622 1.2268 -0.7208 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6089 0.3769 -0.0243 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0698 0.1932 -0.3018 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6141 1.5011 -0.8326 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0984 1.5964 -0.8639 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6886 1.1643 -2.2111 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4317 3.1017 -0.7810 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7841 0.9653 0.2984 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7432 0.6996 1.3954 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8474 -0.4108 0.8051 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0849 -1.0771 1.8968 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7009 -1.5164 1.5551 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9034 -0.3788 1.0404 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5776 0.5027 2.2389 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8317 -1.4247 0.2966 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8680 -1.6661 -0.9162 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6563 -2.0472 1.1998 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4525 0.3655 1.8548 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2776 1.1488 -5.0614 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8529 0.7074 -5.9031 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7982 2.0584 -4.7259 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5561 -1.3615 -1.6928 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0984 -0.5320 -1.5676 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8622 1.8154 -0.8857 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7249 2.2982 0.3785 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1184 1.3817 2.1116 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1200 2.3482 0.9863 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9581 0.2861 -0.0910 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7059 -2.5406 2.6416 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3271 -0.8481 3.2313 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0011 -1.2560 2.7913 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5007 -2.5927 -0.4127 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9692 -1.6141 -0.5309 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8111 -2.8180 0.7506 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8120 -0.3260 1.9492 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4981 -2.5977 -0.0918 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9401 -2.7808 1.6488 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4844 -2.8566 0.9282 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8337 -1.8037 2.2928 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4776 -2.4164 -1.1622 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2393 -0.7735 -1.8313 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1033 -1.6772 -0.9787 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3068 0.7820 1.3033 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6297 2.4433 0.0711 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9933 1.6973 -1.5383 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3523 1.7969 -1.5078 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1928 -0.5189 -1.1859 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2708 1.5799 -1.9142 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1908 2.3737 -0.2913 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7504 2.0164 -2.9186 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7222 0.7833 -2.0750 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0184 0.4186 -2.7027 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1608 3.5116 0.2062 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5195 3.1643 -0.9903 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9158 3.6071 -1.6262 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5774 1.5978 0.7534 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2512 0.0064 0.0267 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1289 1.5863 1.5780 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2087 0.3897 2.3300 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6230 -2.0243 2.2305 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1630 -0.4299 2.8014 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7659 -2.3955 0.9015 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2273 -1.8687 2.5043 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2612 0.0557 2.8501 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4193 0.5002 2.9904 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4356 1.5540 1.9982 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2193 -2.8502 0.9168 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2150 -0.1989 1.5171 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 6 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 10 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 1 29 34 1 6 34 35 2 0 34 36 1 0 9 37 1 0 13 6 1 0 32 16 1 0 18 6 1 0 32 21 1 0 29 22 1 0 1 38 1 0 1 39 1 0 1 40 1 0 5 41 1 0 5 42 1 0 7 43 1 0 7 44 1 0 8 45 1 0 8 46 1 0 9 47 1 6 11 48 1 0 11 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 12 53 1 0 13 54 1 0 14 55 1 0 14 56 1 0 15 57 1 0 15 58 1 0 17 59 1 0 17 60 1 0 17 61 1 0 18 62 1 1 19 63 1 0 19 64 1 0 20 65 1 0 22 66 1 6 23 67 1 0 23 68 1 0 25 69 1 0 25 70 1 0 25 71 1 0 26 72 1 0 26 73 1 0 26 74 1 0 27 75 1 0 27 76 1 0 28 77 1 0 28 78 1 0 30 79 1 0 30 80 1 0 31 81 1 0 31 82 1 0 33 83 1 0 33 84 1 0 33 85 1 0 36 86 1 0 37 87 1 0 M END

Standard InCHIKey	FHWNEUNAQWTXBE-LPRJUICTSA-N
Standard InCHI	InChI=1S/C32H50O5/c1-20(33)37-19-32-13-11-25(34)28(4,5)23(32)10-12-30(7)24(32)9-8-21-22-18-27(2,3)14-16-31(22,26(35)36)17-15-29(21,30)6/h8,22-25,34H,9-19H2,1-7H3,(H,35,36)/t22-,23?,24-,25+,29+,30+,31-,32+/m0/s1
SMILES	CC(=O)OC[C@]12CC[C@H](C(C)(C)C1CC[C@]1(C)[C@@H]2CC=C2[C@@H]3CC(C)(C)CC[C@@]3(CC[C@@]12C)C(=O)O)O

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO40714	Cones liquidamber styraciflua	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15270558]
NPO32560	liquidamber styraciflua	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16441087]

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
GI50	39
ED50	2

Activity Type	# Activity
Cell line	36
Non-molecular	5

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
NPT306	Cell line	PC-3	Homo sapiens	GI50	=	11481.54	nM	PubChem BioAssay data set
NPT90	Cell line	DU-145	Homo sapiens	GI50	=	13182.57	nM	PMID[16562826]
NPT2723	Cell line	MKN-74	Homo sapiens	GI50	=	7762.47	nM	PMID[16562826]
NPT1097	Cell line	MKN-45	Homo sapiens	GI50	=	17782.79	nM	PMID[16562826]
NPT1179	Cell line	MKN-28	Homo sapiens	GI50	=	5623.41	nM	PMID[16562826]
NPT2722	Cell line	St-4	Homo sapiens	GI50	=	9120.11	nM	PMID[16562826]
NPT369	Cell line	ACHN	Homo sapiens	GI50	=	5370.32	nM	PMID[18590312]
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	=	20417.38	nM	PMID[18590312]
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	=	11220.18	nM	PMID[8133298]
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	=	18197.01	nM	PMID[23571415]
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	=	10000.0	nM	PMID[18590312]
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	=	10964.78	nM	PMID[8133298]
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	=	11220.18	nM	PMID[8133298]
NPT576	Cell line	DMS-114	Homo sapiens	GI50	=	13489.63	nM	PMID[22676269]
NPT572	Cell line	DMS-273	Homo sapiens	GI50	=	6309.57	nM	PMID[11087618]
NPT81	Cell line	A549	Homo sapiens	GI50	=	4265.8	nM	PMID[26169123]
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	=	13803.84	nM	PMID[17844994]
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	=	13803.84	nM	PMID[26169123]
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	=	18620.87	nM	PMID[26169123]
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	=	8511.38	nM	PMID[26169123]
NPT393	Cell line	HCT-116	Homo sapiens	GI50	=	4570.88	nM	PMID[17844994]
NPT148	Cell line	HCT-15	Homo sapiens	GI50	=	6456.54	nM	PMID[26169123]
NPT139	Cell line	HT-29	Homo sapiens	GI50	=	3388.44	nM	PMID[26169123]
NPT386	Cell line	KM12	Homo sapiens	GI50	=	5128.61	nM	PMID[26305181]
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	=	28183.83	nM	PMID[26305181]
NPT578	Cell line	SNB-78	Homo sapiens	GI50	=	15848.93	nM	PMID[18314958]
NPT392	Cell line	SNB-75	Homo sapiens	GI50	=	15848.93	nM	PMID[26996372]
NPT374	Cell line	SF-539	Homo sapiens	GI50	=	6309.57	nM	PMID[11520219]
NPT399	Cell line	SF-295	Homo sapiens	GI50	=	8709.64	nM	PMID[23639538]
NPT395	Cell line	SF-268	Homo sapiens	GI50	=	15488.17	nM	PMID[23639538]
NPT380	Cell line	U-251	Homo sapiens	GI50	=	6025.6	nM	PMID[15497935]
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	=	19498.45	nM	PMID[15497935]
NPT83	Cell line	MCF7	Homo sapiens	GI50	=	8317.64	nM	PMID[18980381]
NPT2398	Cell line	MKN-7	Homo sapiens	GI50	=	6606.93	nM	PMID[8984155]
NPT168	Cell line	P388	Mus musculus	ED50	=	28.22	uM	PMID[10924160]
NPT81	Cell line	A549	Homo sapiens	ED50	=	13.31	uM	PMID[10924160]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	10964.78	nM	PMID[15270558]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	11748.98	nM	PMID[15270558]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	10715.19	nM	PMID[15270558]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	7943.28	nM	PMID[15270558]

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 NPC474727 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	17768
0.1-0.2	26545
0.2-0.3	4598
0.3-0.4	624
0.4-0.5	227
0.5-0.6	66
0.6-0.7	19
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
0.7353	Intermediate Similarity	NPC480946
0.7353	Intermediate Similarity	NPC130577
0.7353	Intermediate Similarity	NPC142415
0.7353	Intermediate Similarity	NPC102683
0.6944	Remote Similarity	NPC474963
0.6575	Remote Similarity	NPC298554
0.6528	Remote Similarity	NPC270768
0.6528	Remote Similarity	NPC59263
0.6528	Remote Similarity	NPC210106
0.6301	Remote Similarity	NPC182797
0.6301	Remote Similarity	NPC64872
0.6301	Remote Similarity	NPC84319
0.6301	Remote Similarity	NPC25906
0.6301	Remote Similarity	NPC52021
0.6301	Remote Similarity	NPC52169
0.6301	Remote Similarity	NPC488562
0.6301	Remote Similarity	NPC599947
0.6164	Remote Similarity	NPC198664
0.6	Remote Similarity	NPC231063
0.6	Remote Similarity	NPC282395
0.6	Remote Similarity	NPC158141
0.6	Remote Similarity	NPC481360
0.6	Remote Similarity	NPC110308
0.5921	Remote Similarity	NPC228784
0.5921	Remote Similarity	NPC324341
0.5921	Remote Similarity	NPC120840
0.5921	Remote Similarity	NPC601810
0.5889	Remote Similarity	NPC198621
0.5889	Remote Similarity	NPC216940
0.5867	Remote Similarity	NPC282616
0.5867	Remote Similarity	NPC275809
0.5867	Remote Similarity	NPC156981
0.5789	Remote Similarity	NPC106112
0.5789	Remote Similarity	NPC261935
0.5789	Remote Similarity	NPC130278
0.5733	Remote Similarity	NPC187722
0.5714	Remote Similarity	NPC200752
0.5696	Remote Similarity	NPC296164
0.5676	Remote Similarity	NPC161751
0.5676	Remote Similarity	NPC474972
0.5676	Remote Similarity	NPC600543
0.5667	Remote Similarity	NPC475611
0.5658	Remote Similarity	NPC121798
0.5658	Remote Similarity	NPC234346
0.5641	Remote Similarity	NPC91010
0.5625	Remote Similarity	NPC96580
0.5618	Remote Similarity	NPC284807
0.5616	Remote Similarity	NPC604575
0.5581	Remote Similarity	NPC283849
0.5581	Remote Similarity	NPC28198
0.5581	Remote Similarity	NPC476123
0.5568	Remote Similarity	NPC100383
0.5513	Remote Similarity	NPC202728
0.5513	Remote Similarity	NPC158059
0.5476	Remote Similarity	NPC603645
0.5455	Remote Similarity	NPC51700
0.5455	Remote Similarity	NPC37038
0.5455	Remote Similarity	NPC88716
0.5455	Remote Similarity	NPC68160
0.5455	Remote Similarity	NPC606443
0.5444	Remote Similarity	NPC473538
0.5422	Remote Similarity	NPC481362
0.5385	Remote Similarity	NPC472149
0.5376	Remote Similarity	NPC262970
0.5375	Remote Similarity	NPC130520
0.5325	Remote Similarity	NPC474806
0.5325	Remote Similarity	NPC133579
0.5316	Remote Similarity	NPC139570
0.5316	Remote Similarity	NPC291028
0.5316	Remote Similarity	NPC293564
0.5309	Remote Similarity	NPC222047
0.5287	Remote Similarity	NPC204407
0.5287	Remote Similarity	NPC473576
0.5263	Remote Similarity	NPC280654
0.5256	Remote Similarity	NPC307282
0.5256	Remote Similarity	NPC32118
0.5238	Remote Similarity	NPC188833
0.5227	Remote Similarity	NPC473483
0.5227	Remote Similarity	NPC475570
0.5227	Remote Similarity	NPC606107
0.519	Remote Similarity	NPC609452
0.5161	Remote Similarity	NPC171007
0.5161	Remote Similarity	NPC190849
0.5125	Remote Similarity	NPC29765
0.5111	Remote Similarity	NPC286347
0.5109	Remote Similarity	NPC294112
0.5063	Remote Similarity	NPC229281
0.5059	Remote Similarity	NPC23241
0.5054	Remote Similarity	NPC191410

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5578
0.1-0.2	3480
0.2-0.3	85
0.3-0.4	5
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