NPASS Compound

Natural Product: NPC197272

Natural Product ID	NPC197272
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Petrotriyndiol A
IUPAC Name	(3S,4E,14R,15Z,21Z,27Z,43Z)-hexatetraconta-4,15,21,27,43-pentaen-1,12,45-triyne-3,14-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL447320
PubChem CID	10818083
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

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 120119 0 0 0 0 0 0 0 0999 V2000 16.5198 -0.8237 1.5392 C 0 0 0 0 0 0 0 0 0 0 0 0 15.8576 -1.6331 1.2388 C 0 0 0 0 0 0 0 0 0 0 0 0 14.9527 -2.7296 0.8349 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7918 -2.3507 0.1927 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6413 -0.9153 0.0143 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5404 -0.4438 -1.4566 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6557 1.0762 -1.3653 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6342 1.7895 -0.6136 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2716 1.9397 -1.2134 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3760 2.5829 -0.1500 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0040 1.5908 0.8811 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0385 0.5750 0.2134 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7685 1.3278 -0.0238 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7486 0.5875 -0.7438 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3457 -0.7390 -0.2196 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9692 -0.7068 1.2209 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3928 -2.0807 1.6323 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9793 -2.1070 0.9360 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3234 -0.9800 1.6187 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8656 0.1243 1.1320 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8773 0.5107 -0.2644 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5154 0.7842 -0.8223 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7601 1.8857 -0.1850 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3313 1.7927 1.1940 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6168 0.8271 1.7190 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4895 0.0462 1.1550 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7304 0.0020 -0.2801 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2378 0.4111 -0.4725 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1616 -0.6444 0.0400 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5789 -0.0630 -0.0909 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8953 0.4683 -1.3998 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8278 0.0907 -2.2065 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7644 -1.0077 -1.8953 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3838 -1.0339 -0.6442 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9352 -1.0722 0.5090 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5544 -1.1321 1.8163 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7591 -0.1564 1.7113 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6372 -0.7757 0.6571 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8482 0.0562 0.3891 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5958 0.3157 1.6623 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.9276 1.0236 1.2872 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.6175 -0.0038 0.4824 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.0339 0.1056 -0.7676 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.7008 -1.0326 -1.4353 C 0 0 1 0 0 0 0 0 0 0 0 0 -18.0905 -0.9456 -1.6985 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.3142 -0.8898 -1.9325 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.0381 -1.3074 -2.6817 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1824 -2.2626 -2.2414 O 0 0 0 0 0 0 0 0 0 0 0 0 17.2472 0.0357 1.8544 H 0 0 0 0 0 0 0 0 0 0 0 0 15.1637 -3.7383 1.0205 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1062 -3.0927 -0.1297 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6313 -0.6486 0.4487 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3856 -0.2914 0.5127 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5948 -0.7170 -1.9131 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3857 -0.8215 -2.0326 H 0 0 0 0 0 0 0 0 0 0 0 0 14.6742 1.2546 -0.9175 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6957 1.4131 -2.4433 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5568 1.3565 0.4215 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0011 2.8512 -0.4158 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3033 2.7065 -2.0345 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8672 1.0200 -1.6064 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5466 3.1539 -0.5654 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0689 3.3379 0.3943 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8831 1.0855 1.2893 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4279 2.0628 1.7222 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4218 0.1807 -0.7274 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9535 -0.2580 0.9426 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9901 2.2768 -0.5727 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3950 1.7260 0.9784 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0651 0.5154 -1.8362 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8222 1.2532 -0.8403 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2797 -1.4046 -0.3535 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6190 -1.2401 -0.8951 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8193 -0.4956 1.9031 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2382 0.1092 1.4408 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2424 -2.1158 2.7075 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0366 -2.8368 1.2075 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5788 -3.0855 1.2402 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1197 -2.0558 -0.1126 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2497 -1.1463 2.7379 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4653 0.8061 1.9152 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4661 -0.1876 -0.9210 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4511 1.4854 -0.3929 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0300 -0.2119 -0.8751 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7104 1.0605 -1.9164 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5740 2.7622 -0.1973 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0376 2.3674 -0.8902 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0772 2.0941 1.9283 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3167 2.8579 1.2780 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6027 0.6793 2.8584 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0819 -0.6139 1.8290 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7575 -1.0823 -0.5981 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1485 0.5075 -0.9920 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4356 1.3318 0.1474 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3825 0.5531 -1.5378 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0525 -1.6273 -0.3742 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0174 -0.7553 1.1586 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2208 -0.8784 0.2797 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6553 0.7615 0.6413 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2575 1.3083 -1.7772 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9469 0.6019 -3.2134 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5869 -0.9308 -2.6874 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9511 -0.8835 2.6821 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9850 -2.1673 1.9534 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2214 -0.0569 2.6726 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2907 0.8081 1.3677 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0546 -0.8025 -0.3264 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9145 -1.8172 0.9465 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.4470 -0.5043 -0.3867 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5197 0.9627 -0.1250 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.8824 -0.6088 2.1881 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9836 0.9591 2.3412 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.7202 1.9334 0.7221 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.5016 1.1881 2.2031 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.8241 -0.9840 0.9528 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.8606 1.0273 -1.2886 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.4758 -1.9738 -0.8490 H 0 0 0 0 0 0 0 0 0 0 0 0 -20.3405 -0.8501 -2.1218 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.7778 -1.3731 -3.3743 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2087 -2.2144 -2.3053 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 3 0 2 3 1 0 3 4 2 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 1 0 14 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 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 34 35 3 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 1 0 45 46 3 0 44 47 1 0 33 48 1 0 1 49 1 0 3 50 1 0 4 51 1 0 5 52 1 0 5 53 1 0 6 54 1 0 6 55 1 0 7 56 1 0 7 57 1 0 8 58 1 0 8 59 1 0 9 60 1 0 9 61 1 0 10 62 1 0 10 63 1 0 11 64 1 0 11 65 1 0 12 66 1 0 12 67 1 0 13 68 1 0 13 69 1 0 14 70 1 0 14 71 1 0 15 72 1 0 15 73 1 0 16 74 1 0 16 75 1 0 17 76 1 0 17 77 1 0 18 78 1 0 18 79 1 0 19 80 1 0 20 81 1 0 21 82 1 0 21 83 1 0 22 84 1 0 22 85 1 0 23 86 1 0 23 87 1 0 24 88 1 0 24 89 1 0 25 90 1 0 26 91 1 0 27 92 1 0 27 93 1 0 28 94 1 0 28 95 1 0 29 96 1 0 29 97 1 0 30 98 1 0 30 99 1 0 31100 1 0 32101 1 0 33102 1 6 36103 1 0 36104 1 0 37105 1 0 37106 1 0 38107 1 0 38108 1 0 39109 1 0 39110 1 0 40111 1 0 40112 1 0 41113 1 0 41114 1 0 42115 1 0 43116 1 0 44117 1 1 46118 1 0 47119 1 0 48120 1 0 M END

Standard InCHIKey	RWNBIJPLTYHBMT-AFOSVNONSA-N
Standard InCHI	InChI=1S/C46H72O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-34-37-40-43-46(48)44-41-38-35-32-31-33-36-39-42-45(47)4-2/h1-2,5-6,21-22,27-28,39-40,42-43,45-48H,7-20,23-26,29-38H2/b6-5-,22-21-,28-27-,42-39+,43-40-/t45-,46-/m1/s1
SMILES	C#C/C=CCCCCCCCCCCCCCC/C=CCCCC/C=CCCCC/C=C[C@H](C#CCCCCCC/C=C/[C@@H](C#C)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
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	(15-25 m depth) off Komun Island, Korea	1995-JUL	PMID[10217707]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346968]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170665]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754614]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	Indonesia	1996	PMID[18327911]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	Miyako sea-knoll, southwestern Japan (2525.64' N, 12542.48' E), at a depth of 415 m	2009-OCT	PMID[21534590]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	American Samoa	n.a.	PMID[23368996]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26821210]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917297]
NPO32667	Petrosia sp.	Species	Petrosiidae	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
ED50	5
Inhibition	3

Activity Type	# Activity
Cell line	5
Organism	3

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
NPT81	Cell line	A549	Homo sapiens	ED50	=	1.8	ug ml-1	PMID[20192242]
NPT146	Cell line	SK-OV-3	Homo sapiens	ED50	=	0.8	ug ml-1	PMID[25338277]
NPT147	Cell line	SK-MEL-2	Homo sapiens	ED50	=	0.6	ug ml-1	PMID[16038541]
NPT574	Cell line	XF498	Homo sapiens	ED50	=	1.3	ug ml-1	PMID[18411326]
NPT148	Cell line	HCT-15	Homo sapiens	ED50	=	0.8	ug ml-1	PMID[22037378]
NPT6068	Organism	Simian virus 40	Simian virus 40	Inhibition	=	62.0	%	PMID[17552563]
NPT6068	Organism	Simian virus 40	Simian virus 40	Inhibition	=	90.0	%	PMID[17567121]
NPT6068	Organism	Simian virus 40	Simian virus 40	Inhibition	=	100.0	%	PMID[22769561]

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 NPC197272 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	43339
0.1-0.2	5974
0.2-0.3	415
0.3-0.4	36
0.4-0.5	36
0.5-0.6	21
0.6-0.7	19
0.7-0.8	0
0.8-0.85	1
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8611	High Similarity	NPC89824
0.8611	High Similarity	NPC475477
0.8611	High Similarity	NPC256656
0.8611	High Similarity	NPC294278
0.8611	High Similarity	NPC477723
0.8235	Intermediate Similarity	NPC55383
0.7561	Intermediate Similarity	NPC473896
0.7561	Intermediate Similarity	NPC473735
0.7561	Intermediate Similarity	NPC329608
0.7381	Intermediate Similarity	NPC473847
0.7381	Intermediate Similarity	NPC473721
0.7381	Intermediate Similarity	NPC473725
0.7381	Intermediate Similarity	NPC473910
0.7381	Intermediate Similarity	NPC475384
0.7381	Intermediate Similarity	NPC473532
0.725	Intermediate Similarity	NPC48058
0.7045	Intermediate Similarity	NPC473652
0.6905	Remote Similarity	NPC224148
0.6596	Remote Similarity	NPC168407
0.6579	Remote Similarity	NPC477727
0.6364	Remote Similarity	NPC170776
0.6364	Remote Similarity	NPC9273
0.6364	Remote Similarity	NPC165447
0.6364	Remote Similarity	NPC471959
0.6364	Remote Similarity	NPC199286
0.6364	Remote Similarity	NPC489046
0.6364	Remote Similarity	NPC76198
0.6364	Remote Similarity	NPC610719
0.6341	Remote Similarity	NPC26102
0.6341	Remote Similarity	NPC477724
0.6176	Remote Similarity	NPC607242
0.6136	Remote Similarity	NPC477725
0.6061	Remote Similarity	NPC125122
0.6061	Remote Similarity	NPC471276
0.6061	Remote Similarity	NPC471280
0.6061	Remote Similarity	NPC471281
0.5897	Remote Similarity	NPC161838
0.5833	Remote Similarity	NPC474642
0.5833	Remote Similarity	NPC473913
0.566	Remote Similarity	NPC48968
0.5556	Remote Similarity	NPC249670
0.5532	Remote Similarity	NPC311648
0.5435	Remote Similarity	NPC477726
0.54	Remote Similarity	NPC470967
0.54	Remote Similarity	NPC470968
0.537	Remote Similarity	NPC594
0.5366	Remote Similarity	NPC471960
0.5319	Remote Similarity	NPC470969
0.5294	Remote Similarity	NPC474513
0.5294	Remote Similarity	NPC601905
0.5294	Remote Similarity	NPC603973
0.5238	Remote Similarity	NPC187361
0.52	Remote Similarity	NPC470964
0.5135	Remote Similarity	NPC62779
0.5128	Remote Similarity	NPC329762
0.5128	Remote Similarity	NPC474644
0.5102	Remote Similarity	NPC152668

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC197272 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8661
0.1-0.2	475
0.2-0.3	13
0.3-0.4	1
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