NPASS Compound

Natural Product: NPC327179

Natural Product ID	NPC327179
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta-O-Acetyl-6Beta,19Alpha-Diol-12-Ursen-28-Oic Acid
IUPAC Name	(1R,2R,4aS,6aR,6aS,6bR,8R,8aR,10S,12aR,14bS)-10-acetyloxy-1,8-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms	3-O-acetyluncaricacid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1802043
PubChem CID	53356215
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 88 92 0 0 0 0 0 0 0 0999 V2000 8.1957 -0.6534 -0.1680 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0704 -0.5744 -1.1173 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2858 -0.5150 -2.3375 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7923 -0.5656 -0.6780 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6178 -0.4934 -1.4942 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7937 -1.7226 -1.4120 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4082 -1.6048 -0.9154 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1996 -0.4792 0.1198 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5816 0.7348 -0.6462 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9408 0.8096 -1.2066 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7995 1.5807 -2.5369 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8778 1.7319 -0.4204 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2009 2.0120 0.0761 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8803 2.2720 1.2140 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7002 1.9930 0.1489 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1170 0.8155 0.8942 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7332 -0.4238 0.3647 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2691 -1.5425 1.2758 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1987 -1.5734 1.0982 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9956 -0.5654 0.8522 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3908 0.7790 0.7263 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6697 1.4404 -0.6018 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1617 1.6096 1.7218 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2942 0.9293 2.3848 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2708 0.1757 1.4940 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4513 -0.8488 0.7587 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9673 -1.2595 -0.5729 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1539 -2.7982 -0.7002 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1048 -1.0054 -1.6411 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3771 -0.7649 -0.8458 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7625 -1.2201 -2.2514 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5894 0.6771 -0.6232 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1409 1.0673 0.7332 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1772 -0.4726 2.5338 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3886 -0.2550 2.5901 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6141 -1.3498 3.4628 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3666 1.0536 2.3660 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0590 -0.8365 1.2696 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0937 -1.0301 -0.6523 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3788 0.3489 0.2975 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8528 -1.3169 0.6613 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0376 -0.4512 -2.5246 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7017 -2.2110 -2.4347 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3009 -2.5520 -0.8275 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0852 -2.5746 -0.5471 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7141 -1.3338 -1.7537 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8697 0.7212 -1.5204 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6786 1.4048 -3.1836 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9236 1.1456 -3.1006 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6642 2.6479 -2.3848 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0083 1.4521 0.6108 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5214 2.7851 -0.4555 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8299 1.7446 -1.0287 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4551 2.8247 -0.6385 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8688 3.2263 1.4147 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4537 1.7963 -0.9431 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3764 2.9627 0.5079 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2682 -0.6038 -0.6307 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5326 -1.3086 2.3570 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7280 -2.5038 1.0797 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6755 -2.5723 1.1829 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7598 1.5546 -0.7989 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2603 1.0067 -1.4864 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3240 2.4908 -0.4951 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5851 2.5580 1.2651 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5580 2.0078 2.5676 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9204 1.7290 2.8759 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9808 0.2823 3.2572 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6531 -1.7923 1.3844 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8678 -3.1313 0.0829 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1967 -3.2911 -0.5284 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -2.9789 -1.7133 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3646 -1.6862 -1.6278 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0706 -1.3302 -0.1543 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4536 -0.4570 -2.6512 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3473 -2.1703 -2.2281 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8817 -1.3152 -2.9114 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0251 1.2335 -1.4311 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6725 0.8840 -0.7809 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6119 2.0643 0.6232 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0759 1.3827 1.2984 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1189 -2.1903 3.7621 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2958 0.5090 3.0353 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4457 2.1486 2.5276 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3972 0.7142 2.6748 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5347 -0.0156 1.8018 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4623 -1.4132 2.0015 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8824 -1.5519 0.9810 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 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 9 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 6 27 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 25 34 1 1 34 35 2 0 34 36 1 0 16 37 1 1 8 38 1 1 10 5 1 0 21 16 1 0 33 25 1 0 17 8 1 0 26 20 1 0 1 39 1 0 1 40 1 0 1 41 1 0 5 42 1 6 6 43 1 0 6 44 1 0 7 45 1 0 7 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 6 14 55 1 0 15 56 1 0 15 57 1 0 17 58 1 6 18 59 1 0 18 60 1 0 19 61 1 0 22 62 1 0 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 24 67 1 0 24 68 1 0 26 69 1 1 28 70 1 0 28 71 1 0 28 72 1 0 29 73 1 0 30 74 1 1 31 75 1 0 31 76 1 0 31 77 1 0 32 78 1 0 32 79 1 0 33 80 1 0 33 81 1 0 36 82 1 0 37 83 1 0 37 84 1 0 37 85 1 0 38 86 1 0 38 87 1 0 38 88 1 0 M END

Standard InCHIKey	KBYMABZAFBTCMQ-IQJXLAGFSA-N
Standard InCHI	InChI=1S/C32H50O6/c1-18-11-14-32(26(35)36)16-15-29(6)20(24(32)31(18,8)37)9-10-22-28(5)13-12-23(38-19(2)33)27(3,4)25(28)21(34)17-30(22,29)7/h9,18,21-25,34,37H,10-17H2,1-8H3,(H,35,36)/t18-,21-,22-,23+,24-,25+,28-,29-,30-,31-,32+/m1/s1
SMILES	CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)[C@H](O)C[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@](C)(O)[C@H](C)CC1)C(=O)O)C)C

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
NPO17478	Radermachera boniana	Species	Bignoniaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21469696]
NPO17478	Radermachera boniana	Species	Bignoniaceae	Eukaryota	leaves and twigs	Cuc Phuong National Park (20o 17.901 N, 105o 39.310 E), Ninh Binh, Vietnam	2007-APR	PMID[21469696]
NPO17478	Radermachera boniana	Species	Bignoniaceae	Eukaryota	n.a.	twig	n.a.	PMID[21469696]
NPO17478	Radermachera boniana	Species	Bignoniaceae	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	1

Activity Type	# Activity
Organism	1

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
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	75500.0	nM	PMID[21469696]

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 NPC327179 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	16999
0.1-0.2	26150
0.2-0.3	5801
0.3-0.4	690
0.4-0.5	170
0.5-0.6	34
0.6-0.7	9
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
0.7105	Intermediate Similarity	NPC233012
0.6986	Remote Similarity	NPC118519
0.6892	Remote Similarity	NPC137072
0.6667	Remote Similarity	NPC54909
0.6364	Remote Similarity	NPC157113
0.6184	Remote Similarity	NPC202728
0.6184	Remote Similarity	NPC158059
0.6154	Remote Similarity	NPC187933
0.6026	Remote Similarity	NPC62516
0.6026	Remote Similarity	NPC148964
0.5974	Remote Similarity	NPC259733
0.5974	Remote Similarity	NPC158371
0.5974	Remote Similarity	NPC207922
0.5974	Remote Similarity	NPC136697
0.5897	Remote Similarity	NPC35239
0.5897	Remote Similarity	NPC191412
0.5897	Remote Similarity	NPC114159
0.5897	Remote Similarity	NPC132824
0.5897	Remote Similarity	NPC247139
0.5897	Remote Similarity	NPC6818
0.5867	Remote Similarity	NPC137306
0.5823	Remote Similarity	NPC118964
0.5699	Remote Similarity	NPC482052
0.5684	Remote Similarity	NPC482051
0.5641	Remote Similarity	NPC235053
0.5638	Remote Similarity	NPC25491
0.561	Remote Similarity	NPC603658
0.557	Remote Similarity	NPC256247
0.557	Remote Similarity	NPC120840
0.5556	Remote Similarity	NPC284865
0.5476	Remote Similarity	NPC96693
0.5366	Remote Similarity	NPC147232
0.5366	Remote Similarity	NPC58942
0.5357	Remote Similarity	NPC230151
0.5309	Remote Similarity	NPC485589
0.5287	Remote Similarity	NPC600756
0.5248	Remote Similarity	NPC481234
0.5248	Remote Similarity	NPC479431
0.5244	Remote Similarity	NPC260149
0.5146	Remote Similarity	NPC481235
0.5063	Remote Similarity	NPC43686
0.5062	Remote Similarity	NPC73489
0.5059	Remote Similarity	NPC485586
0.5059	Remote Similarity	NPC485588

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC327179 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5462
0.1-0.2	3579
0.2-0.3	97
0.3-0.4	11
0.4-0.5	1
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