NPASS Compound

Natural Product: NPC290614

Natural Product ID	NPC290614
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Triptocallic Acid A
IUPAC Name	(1R,2R,4S,4aR,6aR,6aS,6bR,8aR,10R,12aR,14bS)-4,10-dihydroxy-1,4a,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL485459
PubChem CID	44575704
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 82 86 0 0 0 0 0 0 0 0999 V2000 -4.4194 3.9787 0.9382 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0945 2.7850 0.7944 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0943 2.5769 1.5201 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7055 1.7190 -0.1779 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6435 0.5618 -0.0740 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0204 -0.6684 0.5161 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8028 -0.4549 1.8621 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7641 -1.0885 -0.2205 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9550 0.0729 -0.7028 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2560 1.4054 -0.0830 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5360 2.4324 -0.9886 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5014 -0.2435 -0.7729 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8265 0.1340 -1.8334 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6267 -0.0998 -2.0628 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2332 -0.1028 -0.6578 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6429 -1.2142 0.1136 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8352 -0.9659 0.3022 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6133 -2.2812 0.4010 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0625 -2.0690 0.6351 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9959 -0.3642 1.6782 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7719 -2.5760 -0.5053 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3308 -1.2800 1.4533 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8612 -1.3596 1.2930 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2301 -0.0204 0.7029 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7079 0.0834 -0.6783 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4440 -0.7381 -1.7007 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9517 1.5448 -1.1026 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3727 1.9767 -0.9348 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0545 1.6207 0.3132 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6639 0.3018 0.9166 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6273 -0.7630 0.5200 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8303 0.5120 2.4346 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9243 2.6808 1.2390 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2943 -1.8745 -1.4376 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3184 4.4341 1.8559 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8968 2.1824 -1.1909 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4845 0.8547 0.5875 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1123 0.3116 -1.0533 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7794 -1.4854 0.4378 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0301 -1.2365 2.4316 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3146 0.2685 -1.7688 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8107 1.6044 0.8986 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8726 3.4625 -0.6852 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4508 2.3288 -0.9380 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9782 2.2906 -1.9953 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3640 0.6751 -2.6572 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0137 0.7116 -2.6736 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8129 -1.0507 -2.6015 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8271 0.8434 -0.2038 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5050 -2.9078 -0.5050 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2531 -2.8930 1.2556 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2231 -1.9267 1.7413 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5262 -3.1017 0.4952 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5929 -1.1304 2.3771 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0574 -0.3103 2.0146 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5925 0.6389 1.7889 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2478 -2.6453 -1.4680 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4394 -3.3022 0.2638 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8198 -2.8693 -0.7136 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0936 -2.1640 2.0482 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1806 -0.3029 1.9666 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2462 -1.4649 2.3277 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1786 -2.2187 0.7197 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6482 0.7325 1.3164 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8095 -0.7780 -2.6103 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8066 -1.7024 -1.3449 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3723 -0.2002 -2.0661 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8065 1.5327 -2.2250 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2488 2.2254 -0.6002 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0249 1.7053 -1.8151 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3410 3.1071 -1.0033 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1649 1.5624 0.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1201 -0.5600 -0.4710 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2270 -1.7936 0.5863 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4984 -0.7495 1.2415 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8105 1.0337 2.5482 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0643 1.1817 2.8329 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9175 -0.4469 2.9631 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8108 3.5411 0.7541 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5240 -2.9163 -1.1706 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2049 -1.4137 -1.8435 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4922 -1.8799 -2.2086 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 9 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 17 20 1 1 16 21 1 6 16 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 29 33 1 0 8 34 1 6 10 4 1 0 17 12 1 0 30 24 1 0 19 8 1 0 25 15 1 0 1 35 1 0 4 36 1 6 5 37 1 0 5 38 1 0 6 39 1 1 7 40 1 0 9 41 1 6 10 42 1 1 11 43 1 0 11 44 1 0 11 45 1 0 13 46 1 0 14 47 1 0 14 48 1 0 15 49 1 1 18 50 1 0 18 51 1 0 19 52 1 0 19 53 1 0 20 54 1 0 20 55 1 0 20 56 1 0 21 57 1 0 21 58 1 0 21 59 1 0 22 60 1 0 22 61 1 0 23 62 1 0 23 63 1 0 24 64 1 1 26 65 1 0 26 66 1 0 26 67 1 0 27 68 1 0 27 69 1 0 28 70 1 0 28 71 1 0 29 72 1 6 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 34 80 1 0 34 81 1 0 34 82 1 0 M END

Standard InCHIKey	IWVWTVWLRSUYNC-BDQDAIHRSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-17-18(25(33)34)16-23(32)28(5)14-15-29(6)19(24(17)28)8-9-21-27(4)12-11-22(31)26(2,3)20(27)10-13-30(21,29)7/h8,17-18,20-24,31-32H,9-16H2,1-7H3,(H,33,34)/t17-,18+,20-,21+,22+,23-,24-,27-,28-,29+,30+/m0/s1
SMILES	OC(=O)[C@@H]1C[C@H](O)[C@]2([C@@H]([C@H]1C)C1=CC[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)CC[C@H](C1(C)C)O)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
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	bark	Leticia, Colombia	n.a.	PMID[15568791]
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14242	Maytenus laevis	Species	Celastraceae	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	6

Activity Type	# Activity
Individual protein	1
Cell line	6

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5212	Individual protein	Sentrin-specific protease 1	Homo sapiens	Inhibition	=	65.5	%	PMID[35500202]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell line	PBMC	Homo sapiens	Activity	=	10.6	pg/ml	PMID[17896816]
NPT927	Cell line	PBMC	Homo sapiens	Activity	=	705.7	pg/ml	PMID[17190448]
NPT927	Cell line	PBMC	Homo sapiens	Activity	<	7.8	pg/ml	PMID[23398362]

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 NPC290614 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	22351
0.1-0.2	23423
0.2-0.3	3118
0.3-0.4	751
0.4-0.5	158
0.5-0.6	41
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	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC18872
0.7778	Intermediate Similarity	NPC610937
0.7463	Intermediate Similarity	NPC105189
0.6377	Remote Similarity	NPC7260
0.6377	Remote Similarity	NPC210037
0.6377	Remote Similarity	NPC120968
0.6377	Remote Similarity	NPC227467
0.6377	Remote Similarity	NPC273621
0.6377	Remote Similarity	NPC112866
0.6094	Remote Similarity	NPC27765
0.6094	Remote Similarity	NPC122418
0.6094	Remote Similarity	NPC491014
0.5915	Remote Similarity	NPC171203
0.5915	Remote Similarity	NPC307426
0.5915	Remote Similarity	NPC98442
0.5915	Remote Similarity	NPC242468
0.5857	Remote Similarity	NPC477872
0.5775	Remote Similarity	NPC480946
0.5775	Remote Similarity	NPC187722
0.5775	Remote Similarity	NPC130577
0.5775	Remote Similarity	NPC142415
0.5775	Remote Similarity	NPC102683
0.5694	Remote Similarity	NPC182797
0.5694	Remote Similarity	NPC51700
0.5694	Remote Similarity	NPC88716
0.5694	Remote Similarity	NPC68160
0.5694	Remote Similarity	NPC52169
0.5694	Remote Similarity	NPC488562
0.5694	Remote Similarity	NPC606443
0.5652	Remote Similarity	NPC95594
0.5634	Remote Similarity	NPC477579
0.5606	Remote Similarity	NPC290598
0.5606	Remote Similarity	NPC30590
0.5588	Remote Similarity	NPC132478
0.5588	Remote Similarity	NPC34177
0.5541	Remote Similarity	NPC202728
0.5541	Remote Similarity	NPC158059
0.5541	Remote Similarity	NPC293564
0.5507	Remote Similarity	NPC235341
0.5507	Remote Similarity	NPC40394
0.5493	Remote Similarity	NPC40552
0.5362	Remote Similarity	NPC101475
0.5342	Remote Similarity	NPC274330
0.5342	Remote Similarity	NPC198664
0.5333	Remote Similarity	NPC228784
0.5333	Remote Similarity	NPC324341
0.5333	Remote Similarity	NPC601810
0.5278	Remote Similarity	NPC246708
0.527	Remote Similarity	NPC142361
0.527	Remote Similarity	NPC474684
0.5147	Remote Similarity	NPC120098
0.5067	Remote Similarity	NPC195019
0.5065	Remote Similarity	NPC263393

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC290614 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6330
0.1-0.2	2759
0.2-0.3	58
0.3-0.4	1
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