NPASS Compound

Natural Product: NPC471333

Natural Product ID	NPC471333
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JTAANBDQXPMQPN-XMSARYDJSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2419286
PubChem CID	73350740
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

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 109112 0 0 0 0 0 0 0 0999 V2000 -4.8880 3.2326 -2.8380 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7727 2.5757 -2.0443 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2324 1.5767 -1.0811 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4792 0.4377 -1.6494 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9795 -0.9037 -1.0860 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5662 0.2772 -3.1554 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1601 0.6491 -1.3475 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0396 1.4619 -0.2423 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3688 2.1377 -0.0044 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1816 3.6326 -0.0515 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9115 1.8617 1.3891 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5613 0.6842 0.9387 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2521 0.0268 0.7858 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1751 -1.2987 0.8617 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0012 -2.3549 1.1179 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3519 -3.5896 0.8871 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1257 -3.3104 0.7993 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1915 -1.8480 0.5985 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5453 -1.3988 -0.7926 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8503 -0.7944 -1.0190 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3641 0.2128 0.0641 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3144 0.3363 1.1291 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0173 0.7954 0.5684 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0770 1.8366 -0.0854 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0870 -1.1220 1.5286 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5977 -1.6020 2.5006 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6087 1.0520 2.3517 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7028 1.4028 2.6889 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5107 1.4304 3.3216 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0757 2.4081 4.3511 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0312 0.2821 4.1060 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6602 -0.3393 0.5955 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6309 1.4500 -0.7244 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1615 2.6725 -0.1461 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5278 2.6639 0.4112 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4532 3.4949 -0.1322 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0967 4.3915 -1.2626 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8146 3.4609 0.4521 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9529 -1.7569 -1.4285 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5306 -2.3697 -2.7441 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2782 -2.1990 -3.8440 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8967 -2.7808 -5.1386 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5181 -1.3935 -3.7103 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7005 -4.6230 1.9194 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0700 -4.8315 1.8810 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9610 -5.8883 1.5971 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3458 -4.2028 3.3194 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9657 2.9575 -2.8535 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5303 2.0848 -2.6915 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3710 3.3617 -1.4994 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1398 1.1411 -0.5573 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1920 -1.6664 -1.2227 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8274 -1.2187 -1.7436 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3747 -0.8281 -0.0798 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5381 0.5631 -3.5824 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4506 -0.8177 -3.4236 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6894 0.7396 -3.6824 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2800 2.2296 -0.4927 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4080 3.9668 -0.7645 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7528 3.9231 0.9556 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1305 4.1925 -0.1171 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9207 2.3707 1.4075 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2946 2.4181 2.1128 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0907 0.8229 1.6219 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6090 1.2912 1.8923 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3508 -0.1039 1.1242 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7160 -3.9707 -0.0920 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5812 -3.8184 -0.0743 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6766 -3.6771 1.6920 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2663 -0.7522 -1.2460 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4751 -2.3293 -1.4187 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7301 -0.1785 -1.9943 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2553 1.9758 2.7467 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1495 3.4398 3.9556 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1281 2.0607 4.5432 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5502 2.3256 5.3115 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7525 -0.2623 4.6770 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6669 0.7392 4.9312 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6073 -0.4534 3.5386 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5182 0.0423 -0.0158 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8242 -0.0413 1.6246 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6723 -1.4588 0.6142 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4195 1.1022 -1.5024 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7551 1.6346 -1.4347 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5206 3.1483 0.6400 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1685 3.4519 -0.9875 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8169 2.0278 1.2332 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3295 5.1395 -0.9666 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7962 3.8025 -2.1617 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9879 4.9731 -1.5722 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8780 2.8929 1.3803 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1537 4.5012 0.6705 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4865 2.9725 -0.3036 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0189 -2.6397 -0.7472 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8812 -1.2279 -1.6053 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6382 -2.9642 -2.8672 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7191 -2.6528 -5.8607 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0037 -2.2767 -5.5546 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6706 -3.8665 -5.0635 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2904 -0.3504 -3.4206 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0259 -1.3216 -4.7112 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2343 -1.9004 -3.0509 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5525 -4.2033 1.3062 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6412 -6.7392 1.8823 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0530 -6.0124 2.2351 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7448 -6.0131 0.5274 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2919 -4.4760 3.5669 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9766 -4.7733 4.0316 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5359 -3.1350 3.5028 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 4 6 1 0 4 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 9 11 1 0 8 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 18 17 1 6 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 22 25 1 0 25 26 2 0 22 27 1 1 27 28 2 0 27 29 1 0 29 30 1 0 29 31 1 0 21 32 1 1 21 33 1 0 33 34 1 0 34 35 1 0 35 36 2 3 36 37 1 0 36 38 1 0 20 39 1 0 39 40 1 0 40 41 2 3 41 42 1 0 41 43 1 0 16 44 1 0 44 45 1 0 44 46 1 0 44 47 1 0 9 3 1 0 23 13 1 0 18 14 1 0 25 18 1 0 1 48 1 0 2 49 1 0 2 50 1 0 3 51 1 1 5 52 1 0 5 53 1 0 5 54 1 0 6 55 1 0 6 56 1 0 6 57 1 0 8 58 1 6 10 59 1 0 10 60 1 0 10 61 1 0 11 62 1 0 11 63 1 0 11 64 1 0 12 65 1 0 12 66 1 0 16 67 1 6 17 68 1 0 17 69 1 0 19 70 1 0 19 71 1 0 20 72 1 6 29 73 1 0 30 74 1 0 30 75 1 0 30 76 1 0 31 77 1 0 31 78 1 0 31 79 1 0 32 80 1 0 32 81 1 0 32 82 1 0 33 83 1 0 33 84 1 0 34 85 1 0 34 86 1 0 35 87 1 0 37 88 1 0 37 89 1 0 37 90 1 0 38 91 1 0 38 92 1 0 38 93 1 0 39 94 1 0 39 95 1 0 40 96 1 0 42 97 1 0 42 98 1 0 42 99 1 0 43100 1 0 43101 1 0 43102 1 0 45103 1 0 46104 1 0 46105 1 0 46106 1 0 47107 1 0 47108 1 0 47109 1 0 M END

Standard InCHIKey	JTAANBDQXPMQPN-XMSARYDJSA-N
Standard InCHI	InChI=1S/C40H62O7/c1-23(2)15-14-18-38(13)26(17-16-24(3)4)20-39-21-30(36(9,10)45)46-33(39)27(32(43)40(38,34(39)44)31(42)25(5)6)19-29-35(7,8)28(22-41)37(11,12)47-29/h15-16,25-26,28-30,41,45H,14,17-22H2,1-13H3/t26-,28+,29+,30-,38+,39-,40-/m0/s1
SMILES	OC[C@H]1C(C)(C)O[C@@H](C1(C)C)CC1=C2O[C@@H](C[C@]32C[C@@H]([C@@]([C@@](C1=O)(C3=O)C(=O)C(C)C)(C)CCC=C(C)C)CC=C(C)C)C(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
NPO33449	hypericum cohaerens	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23957453]
NPO33449	hypericum cohaerens	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
IC50	5

Activity Type	# Activity
Cell line	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
NPT660	Cell line	SW480	Homo sapiens	IC50	=	7400.0	nM	PMID[22676269]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	9300.0	nM	PMID[23163332]
NPT81	Cell line	A549	Homo sapiens	IC50	=	5600.0	nM	PMID[17923491]
NPT659	Cell line	SMMC-7721	Homo sapiens	IC50	=	9500.0	nM	PMID[16562854]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	8800.0	nM	PMID[17958396]

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 NPC471333 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	20957
0.1-0.2	27591
0.2-0.3	1213
0.3-0.4	38
0.4-0.5	28
0.5-0.6	14
0.6-0.7	12
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	NPC471332
0.7681	Intermediate Similarity	NPC471331
0.7681	Intermediate Similarity	NPC99657
0.7681	Intermediate Similarity	NPC203388
0.7317	Intermediate Similarity	NPC144257
0.6986	Remote Similarity	NPC471330
0.6986	Remote Similarity	NPC472687
0.6901	Remote Similarity	NPC483058
0.6757	Remote Similarity	NPC483059
0.6579	Remote Similarity	NPC483057
0.6301	Remote Similarity	NPC472733
0.6301	Remote Similarity	NPC472734
0.6164	Remote Similarity	NPC27105
0.6104	Remote Similarity	NPC483060
0.6081	Remote Similarity	NPC38885
0.6076	Remote Similarity	NPC483061
0.6076	Remote Similarity	NPC483062
0.5714	Remote Similarity	NPC472732
0.5714	Remote Similarity	NPC472731
0.5658	Remote Similarity	NPC472729
0.5658	Remote Similarity	NPC472730
0.5529	Remote Similarity	NPC146239
0.5529	Remote Similarity	NPC483095
0.5443	Remote Similarity	NPC483076
0.5443	Remote Similarity	NPC483078
0.5375	Remote Similarity	NPC483064
0.5375	Remote Similarity	NPC483063
0.5316	Remote Similarity	NPC472728
0.5316	Remote Similarity	NPC472727
0.5057	Remote Similarity	NPC47466
0.5057	Remote Similarity	NPC116274

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471333 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7330
0.1-0.2	1808
0.2-0.3	12
0.3-0.4	0
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