NPASS Compound

Structure

CID318447 OpenBabel06191716142D 53 59 0 0 1 0 0 0 0 0999 V2000 2.3325 2.0985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4776 1.2457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6937 -4.4873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8377 -1.4920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3239 -5.4620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6213 -0.3549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1525 -4.0616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1573 -1.6796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9467 -3.9585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9037 2.3835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7361 -3.5027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1573 -3.5027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1187 1.5876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1070 2.5952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7361 -2.5912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1573 -2.5912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5370 1.0035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5253 2.0111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4621 -2.5543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6588 1.3415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1253 -3.7746 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4313 -0.5761 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2338 -5.4075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2883 0.4936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0538 -3.9257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9467 -2.1354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7402 1.2153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5945 -1.8568 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5843 0.1985 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0046 0.0353 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1394 -3.8314 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8185 -0.0832 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3956 1.4504 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9467 -1.2238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8185 -2.3644 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3678 -1.2238 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5843 -2.6462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9900 0.8596 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5945 -0.5908 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0145 0.8242 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7360 -6.1683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8566 1.2063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6222 -4.6384 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9110 -0.3140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7361 -0.7680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3762 -2.1947 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6416 -4.5922 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3869 0.6295 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3869 -3.0771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5588 1.4356 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1573 -0.7680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0001 0.1461 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 2 0 0 0 0 2 20 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 7 25 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 15 26 2 0 0 0 0 16 26 1 0 0 0 0 17 27 2 0 0 0 0 18 27 1 0 0 0 0 19 21 1 0 0 0 0 19 28 1 0 0 0 0 21 3 1 1 0 0 0 21 31 1 0 0 0 0 22 30 1 0 0 0 0 22 39 1 1 0 0 0 23 41 2 0 0 0 0 23 47 1 0 0 0 0 24 42 2 0 0 0 0 24 48 1 0 0 0 0 25 43 2 0 0 0 0 25 49 1 0 0 0 0 26 34 1 0 0 0 0 27 40 1 0 0 0 0 28 37 1 1 0 0 0 28 39 1 0 0 0 0 29 32 1 0 0 0 0 29 33 1 0 0 0 0 29 39 1 6 0 0 0 30 38 1 1 0 0 0 30 44 1 0 0 0 0 31 37 1 1 0 0 0 31 47 1 0 0 0 0 32 36 1 6 0 0 0 32 48 1 0 0 0 0 33 38 1 1 0 0 0 33 50 1 0 0 0 0 34 45 2 0 0 0 0 34 51 1 0 0 0 0 35 36 1 1 0 0 0 35 37 1 0 0 0 0 35 49 1 0 0 0 0 36 8 1 6 0 0 0 36 51 1 0 0 0 0 37 46 1 1 0 0 0 38 20 1 1 0 0 0 38 52 1 0 0 0 0 39 53 1 1 0 0 0 40 50 1 0 0 0 0 40 52 1 0 0 0 0 40 53 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	734.29
Volume:	725.773
LogP:	4.084
LogD:	2.277
LogS:	-4.067
# Rotatable Bonds:	11
TPSA:	173.35
# H-Bond Aceptor:	13
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.24
Synthetic Accessibility Score:	6.714
Fsp3:	0.55
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.269
MDCK Permeability:	4.799734233529307e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.473
20% Bioavailability (F20%):	0.105
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.301
Plasma Protein Binding (PPB):	78.78898620605469%
Volume Distribution (VD):	2.018
Pgp-substrate:	16.450904846191406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.132
CYP2C9-inhibitor:	0.084
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.444
CYP3A4-substrate:	0.489

ADMET: Excretion

Clearance (CL):	1.996
Half-life (T1/2):	0.281

ADMET: Toxicity

hERG Blockers:	0.551
Human Hepatotoxicity (H-HT):	0.992
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.066
Skin Sensitization:	0.546
Carcinogencity:	0.065
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.965

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC318447

Natural Product ID:	NPC318447
*Common Name:**	Trigoxyphin F
IUPAC Name:	n.a.
Synonyms:	Trigoxyphin F
Standard InCHIKey:	UAEKMRUKSIVWTE-XNFYJXMLSA-N
Standard InCHI:	InChI=1S/C40H46O13/c1-20(2)38-30(44)22(4)39-28-19-21(3)31(47-23(5)41)37(28,46)35(49-25(7)43)36(8,51-34(45)26-15-11-9-12-16-26)32(48-24(6)42)29(39)33(38)50-40(52-38,53-39)27-17-13-10-14-18-27/h9-18,21-22,28-33,35,44,46H,1,19H2,2-8H3/t21-,22+,28+,29-,30-,31-,32-,33+,35+,36+,37+,38-,39-,40?/m0/s1
SMILES:	CC(=O)O[C@H]1[C@H]2[C@H]3OC4(O[C@@]2([C@@H]([C@@H]([C@@]3(O4)C(=C)C)O)C)[C@H]2[C@@]([C@@H]([C@]1(C)OC(=O)c1ccccc1)OC(=O)C)(O)[C@H]([C@H](C2)C)OC(=O)C)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1172567
PubChem CID:	46872821
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003494] Rhamnofolane and daphnane diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO10718	Trigonostemon xyphophylloides	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[20593838]
NPO19424	Trigonostemon howii	Species	Euphorbiaceae	Eukaryota	n.a.	twig	n.a.	PMID[21520897]
NPO19424	Trigonostemon howii	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23148674]
NPO19424	Trigonostemon howii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23215460]
NPO10718	Trigonostemon xyphophylloides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19424	Trigonostemon howii	Species	Euphorbiaceae	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	NP ID	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[549004]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC318447 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	1227
0.2-0.3	2587
0.3-0.4	5395
0.4-0.5	10535
0.5-0.6	14474
0.6-0.7	6861
0.7-0.8	974
0.8-0.85	163
0.85-0.9	112
0.9-0.95	15
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC322048
0.9932	High Similarity	NPC323001
0.9932	High Similarity	NPC326235
0.9865	High Similarity	NPC323356
0.9865	High Similarity	NPC471138
0.9865	High Similarity	NPC326328
0.9865	High Similarity	NPC309991
0.9795	High Similarity	NPC471135
0.9662	High Similarity	NPC290683
0.9662	High Similarity	NPC475638
0.9662	High Similarity	NPC475548
0.9533	High Similarity	NPC319404
0.9474	High Similarity	NPC478124
0.9412	High Similarity	NPC478125
0.9295	High Similarity	NPC40138
0.9252	High Similarity	NPC312393
0.9247	High Similarity	NPC471139
0.9195	High Similarity	NPC476173
0.9161	High Similarity	NPC66193
0.9133	High Similarity	NPC62792
0.9133	High Similarity	NPC478123
0.9128	High Similarity	NPC76103
0.9103	High Similarity	NPC471134
0.906	High Similarity	NPC327031
0.9045	High Similarity	NPC61891
0.9041	High Similarity	NPC325078
0.9007	High Similarity	NPC298072
0.9007	High Similarity	NPC96308
0.8954	High Similarity	NPC34066
0.8926	High Similarity	NPC96903
0.8926	High Similarity	NPC29704
0.8926	High Similarity	NPC472568
0.8926	High Similarity	NPC158663
0.8926	High Similarity	NPC470157
0.8926	High Similarity	NPC174982
0.8926	High Similarity	NPC469349
0.8926	High Similarity	NPC177940
0.8926	High Similarity	NPC200471
0.8926	High Similarity	NPC184817
0.8926	High Similarity	NPC471104
0.8926	High Similarity	NPC171525
0.8926	High Similarity	NPC476973
0.8926	High Similarity	NPC472571
0.8926	High Similarity	NPC472572
0.8926	High Similarity	NPC472575
0.8926	High Similarity	NPC70403
0.8926	High Similarity	NPC473088
0.8926	High Similarity	NPC470159
0.8924	High Similarity	NPC475567
0.8924	High Similarity	NPC325732
0.8924	High Similarity	NPC473468
0.8924	High Similarity	NPC324769
0.8924	High Similarity	NPC473557
0.8903	High Similarity	NPC476784
0.8889	High Similarity	NPC472657
0.8889	High Similarity	NPC472658
0.8868	High Similarity	NPC475531
0.8868	High Similarity	NPC475198
0.8868	High Similarity	NPC475175
0.8867	High Similarity	NPC240115
0.8859	High Similarity	NPC57628
0.8859	High Similarity	NPC95265
0.8859	High Similarity	NPC475122
0.8859	High Similarity	NPC472570
0.8859	High Similarity	NPC25768
0.8859	High Similarity	NPC188865
0.8859	High Similarity	NPC11685
0.8859	High Similarity	NPC95810
0.8859	High Similarity	NPC475759
0.8859	High Similarity	NPC70716
0.8859	High Similarity	NPC472573
0.8859	High Similarity	NPC125106
0.8859	High Similarity	NPC241951
0.8859	High Similarity	NPC470152
0.8859	High Similarity	NPC472569
0.8859	High Similarity	NPC163719
0.8859	High Similarity	NPC476974
0.8854	High Similarity	NPC275477
0.8854	High Similarity	NPC477188
0.8854	High Similarity	NPC477190
0.8854	High Similarity	NPC43304
0.8831	High Similarity	NPC469422
0.8816	High Similarity	NPC469448
0.8808	High Similarity	NPC473760
0.8805	High Similarity	NPC477491
0.8792	High Similarity	NPC163087
0.8784	High Similarity	NPC27377
0.8784	High Similarity	NPC41481
0.8784	High Similarity	NPC472576
0.8784	High Similarity	NPC97947
0.8784	High Similarity	NPC118080
0.8784	High Similarity	NPC16912
0.8784	High Similarity	NPC87448
0.8784	High Similarity	NPC291599
0.875	High Similarity	NPC266265
0.875	High Similarity	NPC301556
0.875	High Similarity	NPC476975
0.875	High Similarity	NPC92293
0.875	High Similarity	NPC471101
0.875	High Similarity	NPC270590
0.8742	High Similarity	NPC474935
0.8742	High Similarity	NPC473602
0.8742	High Similarity	NPC478263
0.8742	High Similarity	NPC209592
0.8742	High Similarity	NPC48599
0.8733	High Similarity	NPC34943
0.8726	High Similarity	NPC477623
0.8716	High Similarity	NPC100913
0.8716	High Similarity	NPC275592
0.8716	High Similarity	NPC171207
0.8716	High Similarity	NPC90614
0.8716	High Similarity	NPC97667
0.8693	High Similarity	NPC473214
0.8693	High Similarity	NPC470245
0.8693	High Similarity	NPC31829
0.8684	High Similarity	NPC281717
0.8679	High Similarity	NPC322420
0.8675	High Similarity	NPC478264
0.8675	High Similarity	NPC472556
0.8662	High Similarity	NPC49297
0.8662	High Similarity	NPC469399
0.8658	High Similarity	NPC266374
0.8654	High Similarity	NPC154675
0.8642	High Similarity	NPC477488
0.8636	High Similarity	NPC470153
0.8636	High Similarity	NPC469415
0.8627	High Similarity	NPC473215
0.8618	High Similarity	NPC20255
0.86	High Similarity	NPC192658
0.8599	High Similarity	NPC181924
0.8591	High Similarity	NPC48017
0.8591	High Similarity	NPC200592
0.8591	High Similarity	NPC147880
0.8591	High Similarity	NPC43241
0.8591	High Similarity	NPC473613
0.8591	High Similarity	NPC211137
0.8591	High Similarity	NPC473109
0.8591	High Similarity	NPC473112
0.8591	High Similarity	NPC184747
0.8591	High Similarity	NPC476094
0.8591	High Similarity	NPC473081
0.8591	High Similarity	NPC4341
0.8591	High Similarity	NPC473085
0.8591	High Similarity	NPC473758
0.8591	High Similarity	NPC473060
0.859	High Similarity	NPC469398
0.8581	High Similarity	NPC472548
0.8581	High Similarity	NPC477905
0.8571	High Similarity	NPC303429
0.8571	High Similarity	NPC475417
0.8571	High Similarity	NPC222102
0.8571	High Similarity	NPC475561
0.8553	High Similarity	NPC92867
0.8553	High Similarity	NPC311825
0.8553	High Similarity	NPC125882
0.8543	High Similarity	NPC131966
0.8543	High Similarity	NPC91703
0.8543	High Similarity	NPC191387
0.8533	High Similarity	NPC224491
0.8523	High Similarity	NPC475652
0.8523	High Similarity	NPC214550
0.8523	High Similarity	NPC210591
0.85	High Similarity	NPC55744
0.8481	Intermediate Similarity	NPC469417
0.8477	Intermediate Similarity	NPC34012
0.8471	Intermediate Similarity	NPC473611
0.8471	Intermediate Similarity	NPC472549
0.8471	Intermediate Similarity	NPC469456
0.8471	Intermediate Similarity	NPC473632
0.8471	Intermediate Similarity	NPC469730
0.8471	Intermediate Similarity	NPC132599
0.8467	Intermediate Similarity	NPC472547
0.8467	Intermediate Similarity	NPC87934
0.8467	Intermediate Similarity	NPC162613
0.8456	Intermediate Similarity	NPC183122
0.8456	Intermediate Similarity	NPC283375
0.8446	Intermediate Similarity	NPC291638
0.8446	Intermediate Similarity	NPC17877
0.8446	Intermediate Similarity	NPC195647
0.8446	Intermediate Similarity	NPC472577
0.8446	Intermediate Similarity	NPC66761
0.8421	Intermediate Similarity	NPC191082
0.8421	Intermediate Similarity	NPC475429
0.8421	Intermediate Similarity	NPC473673
0.8421	Intermediate Similarity	NPC139067
0.8421	Intermediate Similarity	NPC177340
0.8421	Intermediate Similarity	NPC270498
0.8421	Intermediate Similarity	NPC246480
0.8421	Intermediate Similarity	NPC147217
0.8418	Intermediate Similarity	NPC106895
0.8418	Intermediate Similarity	NPC70344
0.8412	Intermediate Similarity	NPC186746
0.8408	Intermediate Similarity	NPC146310
0.8408	Intermediate Similarity	NPC469477
0.8408	Intermediate Similarity	NPC133430
0.84	Intermediate Similarity	NPC121268
0.84	Intermediate Similarity	NPC9905
0.84	Intermediate Similarity	NPC53361
0.84	Intermediate Similarity	NPC473301
0.8378	Intermediate Similarity	NPC474608

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC318447 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	763
0.2-0.3	1598
0.3-0.4	3065
0.4-0.5	2344
0.5-0.6	897
0.6-0.7	191
0.7-0.8	13
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8364	Intermediate Similarity	NPD7799	Discontinued
0.7977	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD7236	Approved
0.7826	Intermediate Similarity	NPD7239	Suspended
0.7778	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7685	Pre-registration
0.7632	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8407	Phase 2
0.7443	Intermediate Similarity	NPD8368	Discontinued
0.7396	Intermediate Similarity	NPD7058	Phase 2
0.7396	Intermediate Similarity	NPD7057	Phase 3
0.7372	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD8435	Approved
0.7348	Intermediate Similarity	NPD8360	Approved
0.7348	Intermediate Similarity	NPD8361	Approved
0.7315	Intermediate Similarity	NPD5126	Approved
0.7315	Intermediate Similarity	NPD5125	Phase 3
0.7314	Intermediate Similarity	NPD7228	Approved
0.7294	Intermediate Similarity	NPD4967	Phase 2
0.7294	Intermediate Similarity	NPD4965	Approved
0.7294	Intermediate Similarity	NPD4966	Approved
0.7268	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8434	Phase 2
0.7238	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8127	Discontinued
0.7225	Intermediate Similarity	NPD7199	Phase 2
0.7219	Intermediate Similarity	NPD37	Approved
0.7209	Intermediate Similarity	NPD6234	Discontinued
0.7169	Intermediate Similarity	NPD6273	Approved
0.7167	Intermediate Similarity	NPD8313	Approved
0.7167	Intermediate Similarity	NPD8312	Approved
0.7158	Intermediate Similarity	NPD7497	Discontinued
0.7151	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD8150	Discontinued
0.709	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5844	Phase 1
0.7076	Intermediate Similarity	NPD8455	Phase 2
0.7067	Intermediate Similarity	NPD7741	Discontinued
0.7045	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7266	Discontinued
0.6981	Remote Similarity	NPD7961	Discontinued
0.6977	Remote Similarity	NPD5760	Phase 2
0.6977	Remote Similarity	NPD5761	Phase 2
0.6973	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6559	Discontinued
0.6931	Remote Similarity	NPD8485	Approved
0.6928	Remote Similarity	NPD6190	Approved
0.6918	Remote Similarity	NPD3764	Approved
0.6901	Remote Similarity	NPD7028	Phase 2
0.6897	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7699	Phase 2
0.6895	Remote Similarity	NPD7700	Phase 2
0.6887	Remote Similarity	NPD7516	Approved
0.6879	Remote Similarity	NPD7819	Suspended
0.6868	Remote Similarity	NPD6764	Approved
0.6868	Remote Similarity	NPD6765	Approved
0.6867	Remote Similarity	NPD4628	Phase 3
0.6857	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD8319	Approved
0.6856	Remote Similarity	NPD8320	Phase 1
0.6855	Remote Similarity	NPD7008	Discontinued
0.6845	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7458	Discontinued
0.6842	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7507	Approved
0.6825	Remote Similarity	NPD6534	Approved
0.6825	Remote Similarity	NPD6535	Approved
0.6824	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7328	Approved
0.6821	Remote Similarity	NPD7327	Approved
0.6815	Remote Similarity	NPD7319	Approved
0.6805	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7435	Discontinued
0.6802	Remote Similarity	NPD4380	Phase 2
0.6796	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6002	Phase 3
0.6788	Remote Similarity	NPD5762	Approved
0.6788	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5763	Approved
0.6788	Remote Similarity	NPD6005	Phase 3
0.6788	Remote Similarity	NPD6004	Phase 3
0.6784	Remote Similarity	NPD8462	Phase 1
0.6782	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6663	Approved
0.6766	Remote Similarity	NPD8166	Discontinued
0.6761	Remote Similarity	NPD7075	Discontinued
0.6758	Remote Similarity	NPD7074	Phase 3
0.6757	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.674	Remote Similarity	NPD3818	Discontinued
0.6721	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6784	Approved
0.672	Remote Similarity	NPD6785	Approved
0.6706	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7054	Approved
0.6689	Remote Similarity	NPD2629	Approved
0.6688	Remote Similarity	NPD8380	Approved
0.6688	Remote Similarity	NPD8335	Approved
0.6688	Remote Similarity	NPD8378	Approved
0.6688	Remote Similarity	NPD8033	Approved
0.6688	Remote Similarity	NPD8379	Approved
0.6688	Remote Similarity	NPD8296	Approved
0.6687	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7473	Discontinued
0.6685	Remote Similarity	NPD5494	Approved
0.6683	Remote Similarity	NPD7874	Approved
0.6683	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6823	Phase 2
0.6667	Remote Similarity	NPD7094	Approved
0.6667	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD6858	Approved
0.665	Remote Similarity	NPD7999	Approved
0.6649	Remote Similarity	NPD6776	Approved
0.6649	Remote Similarity	NPD6782	Approved
0.6649	Remote Similarity	NPD6777	Approved
0.6649	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7808	Phase 3
0.6649	Remote Similarity	NPD6778	Approved
0.6649	Remote Similarity	NPD6781	Approved
0.6649	Remote Similarity	NPD6780	Approved
0.6649	Remote Similarity	NPD6779	Approved
0.6648	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5402	Approved
0.6648	Remote Similarity	NPD3751	Discontinued
0.6645	Remote Similarity	NPD4198	Discontinued
0.6633	Remote Similarity	NPD7696	Phase 3
0.6633	Remote Similarity	NPD7698	Approved
0.6633	Remote Similarity	NPD7697	Approved
0.6633	Remote Similarity	NPD7680	Approved
0.6627	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD5736	Approved
0.6623	Remote Similarity	NPD8377	Approved
0.6623	Remote Similarity	NPD8294	Approved
0.6611	Remote Similarity	NPD6232	Discontinued
0.6611	Remote Similarity	NPD3787	Discontinued
0.661	Remote Similarity	NPD7768	Phase 2
0.6606	Remote Similarity	NPD7097	Phase 1
0.6599	Remote Similarity	NPD7870	Phase 2
0.6599	Remote Similarity	NPD6685	Approved
0.6599	Remote Similarity	NPD7871	Phase 2
0.6598	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD7251	Discontinued
0.6585	Remote Similarity	NPD6355	Discontinued
0.6583	Remote Similarity	NPD7701	Phase 2
0.6581	Remote Similarity	NPD7503	Approved
0.6579	Remote Similarity	NPD5951	Approved
0.6571	Remote Similarity	NPD7411	Suspended
0.6567	Remote Similarity	NPD7801	Approved
0.6558	Remote Similarity	NPD7610	Discontinued
0.6552	Remote Similarity	NPD7930	Approved
0.655	Remote Similarity	NPD8151	Discontinued
0.6541	Remote Similarity	NPD7736	Approved
0.6541	Remote Similarity	NPD6797	Phase 2
0.6538	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6166	Phase 2
0.6538	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD6801	Discontinued
0.6532	Remote Similarity	NPD5403	Approved
0.6512	Remote Similarity	NPD5401	Approved
0.651	Remote Similarity	NPD6213	Phase 3
0.651	Remote Similarity	NPD2182	Approved
0.651	Remote Similarity	NPD6212	Phase 3
0.651	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6674	Discontinued
0.6509	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD8404	Phase 2
0.6488	Remote Similarity	NPD2346	Discontinued
0.6485	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD5735	Approved
0.6485	Remote Similarity	NPD7783	Phase 2
0.6471	Remote Similarity	NPD7003	Approved
0.6471	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3750	Approved
0.6461	Remote Similarity	NPD3817	Phase 2
0.646	Remote Similarity	NPD6085	Phase 2
0.646	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD3226	Approved
0.6448	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6653	Approved
0.6444	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD1934	Approved
0.6433	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5405	Approved
0.6429	Remote Similarity	NPD5408	Approved
0.6429	Remote Similarity	NPD2935	Discontinued
0.6429	Remote Similarity	NPD5404	Approved
0.6429	Remote Similarity	NPD7137	Phase 2
0.6429	Remote Similarity	NPD5406	Approved
0.6424	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD4140	Approved
0.642	Remote Similarity	NPD6599	Discontinued
0.6416	Remote Similarity	NPD2532	Approved
0.6416	Remote Similarity	NPD2534	Approved
0.6416	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD2533	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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