NPASS Compound

Structure

CID323356 OpenBabel06191716172D 43 50 0 0 1 0 0 0 0 0999 V2000 2.0777 1.8345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9410 1.1506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7031 -4.0719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6768 -1.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3179 -1.9509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6915 -2.2092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9937 1.7935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8567 -1.4774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9752 -2.4321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3661 2.2046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9514 1.0445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3055 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4240 -1.9232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6963 1.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2816 0.7066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4614 -2.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4408 1.1781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1745 -3.4326 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2931 -0.5471 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5891 -1.1914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6541 1.1177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5112 -1.6991 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4447 0.1552 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9754 -3.5045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8245 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5633 -0.1209 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2931 1.2973 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0379 -0.6824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5267 -2.1966 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0448 -1.1675 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3991 -2.4332 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8245 0.7502 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5314 -0.5471 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.7502 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.4201 -4.2048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2031 0.0494 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0324 -2.8542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1270 -2.0351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6053 -1.1282 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7105 -0.2272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5314 1.2973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9124 0.1170 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 17 2 0 0 0 0 2 17 1 0 0 0 0 4 19 1 0 0 0 0 6 8 2 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 20 2 0 0 0 0 13 20 1 0 0 0 0 14 21 2 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 22 1 0 0 0 0 18 3 1 1 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 19 33 1 1 0 0 0 20 28 1 0 0 0 0 21 34 1 0 0 0 0 22 31 1 1 0 0 0 22 33 1 0 0 0 0 23 26 1 0 0 0 0 23 27 1 0 0 0 0 23 33 1 6 0 0 0 24 31 1 1 0 0 0 24 35 1 0 0 0 0 25 32 1 1 0 0 0 25 39 1 0 0 0 0 26 30 1 6 0 0 0 26 40 1 0 0 0 0 27 32 1 1 0 0 0 27 41 1 0 0 0 0 28 36 2 0 0 0 0 28 39 1 0 0 0 0 29 30 1 1 0 0 0 29 31 1 0 0 0 0 29 37 1 0 0 0 0 30 5 1 1 0 0 0 30 40 1 0 0 0 0 31 38 1 1 0 0 0 32 17 1 1 0 0 0 32 42 1 0 0 0 0 33 43 1 1 0 0 0 34 41 1 0 0 0 0 34 42 1 0 0 0 0 34 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	590.25
Volume:	586.189
LogP:	4.335
LogD:	3.441
LogS:	-4.237
# Rotatable Bonds:	5
TPSA:	127.21
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.28
Synthetic Accessibility Score:	6.478
Fsp3:	0.559
Lipinski Rule-of-5:	Accepted
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:	-5.229
MDCK Permeability:	4.993129550712183e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.444
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.468
Plasma Protein Binding (PPB):	92.6280746459961%
Volume Distribution (VD):	1.702
Pgp-substrate:	3.9277243614196777%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.943
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.544
CYP2C9-inhibitor:	0.204
CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.186
CYP3A4-inhibitor:	0.121
CYP3A4-substrate:	0.395

ADMET: Excretion

Clearance (CL):	6.244
Half-life (T1/2):	0.662

ADMET: Toxicity

hERG Blockers:	0.601
Human Hepatotoxicity (H-HT):	0.978
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.147
Rat Oral Acute Toxicity:	0.512
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.6
Carcinogencity:	0.152
Eye Corrosion:	0.004
Eye Irritation:	0.04
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC323356

Natural Product ID:	NPC323356
*Common Name:**	Trigonosin A
IUPAC Name:	n.a.
Synonyms:	Trigonosin A
Standard InCHIKey:	VOVLVSQLMDTVFG-IHORLDMESA-N
Standard InCHI:	InChI=1S/C34H38O9/c1-17(2)32-25(39-28(36)20-12-8-6-9-13-20)19(4)33-22-16-18(3)24(35)31(22,38)29(37)30(5)26(40-30)23(33)27(32)41-34(42-32,43-33)21-14-10-7-11-15-21/h6-15,18-19,22-27,29,35,37-38H,1,16H2,2-5H3/t18-,19+,22+,23-,24-,25-,26-,27+,29+,30-,31+,32-,33-,34?/m0/s1
SMILES:	CC1CC2C34C(C(C5(C(C3C6C(O6)(C(C2(C1O)O)O)C)OC(O4)(O5)C7=CC=CC=C7)C(=C)C)OC(=O)C8=CC=CC=C8)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1765392
PubChem CID:	52936751
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
NPO31570	Trigonostemon thyrsoideum	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[21192108]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[573983]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[573983]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[573983]

☑ 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 NPC323356 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	358
0.1-0.2	1241
0.2-0.3	2675
0.3-0.4	5541
0.4-0.5	10754
0.5-0.6	14811
0.6-0.7	6146
0.7-0.8	882
0.8-0.85	162
0.85-0.9	93
0.9-0.95	12
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC326328
1.0	High Similarity	NPC309991
1.0	High Similarity	NPC471138
0.9865	High Similarity	NPC322048
0.9865	High Similarity	NPC318447
0.9797	High Similarity	NPC290683
0.9797	High Similarity	NPC323001
0.9797	High Similarity	NPC475638
0.9797	High Similarity	NPC326235
0.9797	High Similarity	NPC475548
0.9662	High Similarity	NPC471135
0.9605	High Similarity	NPC478124
0.9542	High Similarity	NPC478125
0.9423	High Similarity	NPC40138
0.9408	High Similarity	NPC319404
0.9267	High Similarity	NPC478123
0.9267	High Similarity	NPC62792
0.9172	High Similarity	NPC61891
0.9139	High Similarity	NPC298072
0.9128	High Similarity	NPC312393
0.9122	High Similarity	NPC471139
0.9073	High Similarity	NPC476173
0.9051	High Similarity	NPC324769
0.9051	High Similarity	NPC325732
0.9045	High Similarity	NPC66193
0.9007	High Similarity	NPC76103
0.8987	High Similarity	NPC471134
0.8981	High Similarity	NPC275477
0.8981	High Similarity	NPC477188
0.8981	High Similarity	NPC477190
0.8981	High Similarity	NPC43304
0.894	High Similarity	NPC327031
0.8931	High Similarity	NPC477491
0.8919	High Similarity	NPC325078
0.8896	High Similarity	NPC472657
0.8896	High Similarity	NPC472658
0.8889	High Similarity	NPC96308
0.8839	High Similarity	NPC34066
0.8812	High Similarity	NPC473557
0.8812	High Similarity	NPC473468
0.8812	High Similarity	NPC475567
0.8808	High Similarity	NPC472575
0.8808	High Similarity	NPC470159
0.8808	High Similarity	NPC70403
0.8808	High Similarity	NPC472568
0.8808	High Similarity	NPC158663
0.8808	High Similarity	NPC184817
0.8808	High Similarity	NPC469349
0.8808	High Similarity	NPC471104
0.8808	High Similarity	NPC174982
0.8808	High Similarity	NPC470157
0.8808	High Similarity	NPC473088
0.8808	High Similarity	NPC472572
0.8808	High Similarity	NPC177940
0.8808	High Similarity	NPC96903
0.8808	High Similarity	NPC171525
0.8808	High Similarity	NPC476973
0.8808	High Similarity	NPC472571
0.8808	High Similarity	NPC29704
0.8808	High Similarity	NPC200471
0.8805	High Similarity	NPC322420
0.879	High Similarity	NPC476784
0.879	High Similarity	NPC49297
0.8782	High Similarity	NPC154675
0.8765	High Similarity	NPC477488
0.8758	High Similarity	NPC475531
0.8758	High Similarity	NPC475175
0.8758	High Similarity	NPC475198
0.875	High Similarity	NPC240115
0.8742	High Similarity	NPC95810
0.8742	High Similarity	NPC188865
0.8742	High Similarity	NPC11685
0.8742	High Similarity	NPC476974
0.8742	High Similarity	NPC472570
0.8742	High Similarity	NPC125106
0.8742	High Similarity	NPC25768
0.8742	High Similarity	NPC470152
0.8742	High Similarity	NPC163719
0.8742	High Similarity	NPC475122
0.8742	High Similarity	NPC475759
0.8742	High Similarity	NPC57628
0.8742	High Similarity	NPC472569
0.8742	High Similarity	NPC241951
0.8742	High Similarity	NPC95265
0.8742	High Similarity	NPC70716
0.8742	High Similarity	NPC472573
0.8726	High Similarity	NPC181924
0.8718	High Similarity	NPC469422
0.8701	High Similarity	NPC469448
0.8693	High Similarity	NPC473760
0.8675	High Similarity	NPC163087
0.8667	High Similarity	NPC472576
0.8667	High Similarity	NPC118080
0.8667	High Similarity	NPC27377
0.8667	High Similarity	NPC41481
0.8667	High Similarity	NPC87448
0.8667	High Similarity	NPC97947
0.8667	High Similarity	NPC16912
0.8667	High Similarity	NPC291599
0.8636	High Similarity	NPC476975
0.8636	High Similarity	NPC92293
0.8636	High Similarity	NPC266265
0.8636	High Similarity	NPC301556
0.8636	High Similarity	NPC471101
0.8636	High Similarity	NPC270590
0.8627	High Similarity	NPC474935
0.8627	High Similarity	NPC48599
0.8627	High Similarity	NPC209592
0.8627	High Similarity	NPC473602
0.8627	High Similarity	NPC478263
0.8618	High Similarity	NPC34943
0.8616	High Similarity	NPC477623
0.86	High Similarity	NPC100913
0.86	High Similarity	NPC171207
0.86	High Similarity	NPC97667
0.86	High Similarity	NPC275592
0.86	High Similarity	NPC90614
0.8581	High Similarity	NPC473214
0.8581	High Similarity	NPC475417
0.8581	High Similarity	NPC470245
0.8581	High Similarity	NPC31829
0.8581	High Similarity	NPC475561
0.8571	High Similarity	NPC281717
0.8562	High Similarity	NPC472556
0.8562	High Similarity	NPC478264
0.8553	High Similarity	NPC191387
0.8553	High Similarity	NPC131966
0.8553	High Similarity	NPC469399
0.8543	High Similarity	NPC266374
0.8535	High Similarity	NPC146310
0.8529	High Similarity	NPC186746
0.8526	High Similarity	NPC470153
0.8526	High Similarity	NPC469415
0.8516	High Similarity	NPC473215
0.8506	High Similarity	NPC20255
0.8487	Intermediate Similarity	NPC192658
0.8481	Intermediate Similarity	NPC469398
0.8481	Intermediate Similarity	NPC251139
0.8477	Intermediate Similarity	NPC43241
0.8477	Intermediate Similarity	NPC48017
0.8477	Intermediate Similarity	NPC147880
0.8477	Intermediate Similarity	NPC473613
0.8477	Intermediate Similarity	NPC473085
0.8477	Intermediate Similarity	NPC473060
0.8477	Intermediate Similarity	NPC473112
0.8477	Intermediate Similarity	NPC184747
0.8477	Intermediate Similarity	NPC476094
0.8477	Intermediate Similarity	NPC473109
0.8477	Intermediate Similarity	NPC473081
0.8477	Intermediate Similarity	NPC211137
0.8477	Intermediate Similarity	NPC473758
0.8477	Intermediate Similarity	NPC4341
0.8477	Intermediate Similarity	NPC200592
0.8471	Intermediate Similarity	NPC472548
0.8471	Intermediate Similarity	NPC477905
0.8462	Intermediate Similarity	NPC222102
0.8462	Intermediate Similarity	NPC303429
0.8442	Intermediate Similarity	NPC92867
0.8442	Intermediate Similarity	NPC125882
0.8442	Intermediate Similarity	NPC311825
0.8431	Intermediate Similarity	NPC91703
0.8421	Intermediate Similarity	NPC224491
0.8411	Intermediate Similarity	NPC210591
0.8411	Intermediate Similarity	NPC475652
0.8411	Intermediate Similarity	NPC214550
0.8395	Intermediate Similarity	NPC55744
0.8375	Intermediate Similarity	NPC469417
0.8366	Intermediate Similarity	NPC34012
0.8365	Intermediate Similarity	NPC469730
0.8365	Intermediate Similarity	NPC472549
0.8365	Intermediate Similarity	NPC471176
0.8365	Intermediate Similarity	NPC132599
0.8365	Intermediate Similarity	NPC469456
0.8365	Intermediate Similarity	NPC473611
0.8365	Intermediate Similarity	NPC473632
0.8355	Intermediate Similarity	NPC472547
0.8355	Intermediate Similarity	NPC87934
0.8355	Intermediate Similarity	NPC162613
0.8344	Intermediate Similarity	NPC283375
0.8344	Intermediate Similarity	NPC183122
0.8333	Intermediate Similarity	NPC291638
0.8333	Intermediate Similarity	NPC66761
0.8333	Intermediate Similarity	NPC17877
0.8333	Intermediate Similarity	NPC472577
0.8333	Intermediate Similarity	NPC195647
0.8313	Intermediate Similarity	NPC70344
0.8313	Intermediate Similarity	NPC106895
0.8312	Intermediate Similarity	NPC270498
0.8312	Intermediate Similarity	NPC246480
0.8312	Intermediate Similarity	NPC473673
0.8312	Intermediate Similarity	NPC139067
0.8312	Intermediate Similarity	NPC147217
0.8312	Intermediate Similarity	NPC191082
0.8312	Intermediate Similarity	NPC177340
0.8312	Intermediate Similarity	NPC475429
0.8312	Intermediate Similarity	NPC477894
0.8304	Intermediate Similarity	NPC254588
0.8302	Intermediate Similarity	NPC133430
0.8302	Intermediate Similarity	NPC469477
0.8289	Intermediate Similarity	NPC53361

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 NPC323356 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	781
0.2-0.3	1683
0.3-0.4	3109
0.4-0.5	2264
0.5-0.6	839
0.6-0.7	175
0.7-0.8	11
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
0.8263	Intermediate Similarity	NPD7799	Discontinued
0.7886	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD7236	Approved
0.7759	Intermediate Similarity	NPD7685	Pre-registration
0.773	Intermediate Similarity	NPD7239	Suspended
0.7688	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8407	Phase 2
0.736	Intermediate Similarity	NPD8368	Discontinued
0.731	Intermediate Similarity	NPD7057	Phase 3
0.731	Intermediate Similarity	NPD7058	Phase 2
0.7278	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8361	Approved
0.7268	Intermediate Similarity	NPD8360	Approved
0.7268	Intermediate Similarity	NPD8435	Approved
0.7253	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7228	Approved
0.7219	Intermediate Similarity	NPD5125	Phase 3
0.7219	Intermediate Similarity	NPD5126	Approved
0.7209	Intermediate Similarity	NPD4967	Phase 2
0.7209	Intermediate Similarity	NPD4965	Approved
0.7209	Intermediate Similarity	NPD4966	Approved
0.7189	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD7199	Phase 2
0.7135	Intermediate Similarity	NPD37	Approved
0.7126	Intermediate Similarity	NPD6234	Discontinued
0.7088	Intermediate Similarity	NPD8312	Approved
0.7088	Intermediate Similarity	NPD8313	Approved
0.7083	Intermediate Similarity	NPD7497	Discontinued
0.7083	Intermediate Similarity	NPD6273	Approved
0.7072	Intermediate Similarity	NPD7240	Approved
0.7065	Intermediate Similarity	NPD8150	Discontinued
0.7016	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5844	Phase 1
0.6994	Remote Similarity	NPD8455	Phase 2
0.6974	Remote Similarity	NPD7741	Discontinued
0.6966	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7266	Discontinued
0.6898	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5760	Phase 2
0.6897	Remote Similarity	NPD5761	Phase 2
0.6894	Remote Similarity	NPD7961	Discontinued
0.6885	Remote Similarity	NPD6559	Discontinued
0.6859	Remote Similarity	NPD8485	Approved
0.6845	Remote Similarity	NPD6190	Approved
0.6832	Remote Similarity	NPD3764	Approved
0.6823	Remote Similarity	NPD7699	Phase 2
0.6823	Remote Similarity	NPD7700	Phase 2
0.6821	Remote Similarity	NPD7028	Phase 2
0.6818	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7819	Suspended
0.6797	Remote Similarity	NPD7516	Approved
0.6793	Remote Similarity	NPD6764	Approved
0.6793	Remote Similarity	NPD6765	Approved
0.6786	Remote Similarity	NPD4628	Phase 3
0.6786	Remote Similarity	NPD8320	Phase 1
0.6786	Remote Similarity	NPD8319	Approved
0.678	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7008	Discontinued
0.6765	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7458	Discontinued
0.6758	Remote Similarity	NPD3751	Discontinued
0.6754	Remote Similarity	NPD6535	Approved
0.6754	Remote Similarity	NPD6534	Approved
0.6752	Remote Similarity	NPD7507	Approved
0.6751	Remote Similarity	NPD7999	Approved
0.6744	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7435	Discontinued
0.6732	Remote Similarity	NPD7327	Approved
0.6732	Remote Similarity	NPD7328	Approved
0.673	Remote Similarity	NPD7319	Approved
0.6725	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4380	Phase 2
0.6722	Remote Similarity	NPD3787	Discontinued
0.6721	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD8462	Phase 1
0.6707	Remote Similarity	NPD6004	Phase 3
0.6707	Remote Similarity	NPD6002	Phase 3
0.6707	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5762	Approved
0.6707	Remote Similarity	NPD6005	Phase 3
0.6707	Remote Similarity	NPD5763	Approved
0.6705	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6663	Approved
0.6686	Remote Similarity	NPD8166	Discontinued
0.6685	Remote Similarity	NPD7075	Discontinued
0.6685	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7930	Approved
0.6649	Remote Similarity	NPD6784	Approved
0.6649	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6785	Approved
0.663	Remote Similarity	NPD7054	Approved
0.6628	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7874	Approved
0.6617	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7473	Discontinued
0.6611	Remote Similarity	NPD5494	Approved
0.6607	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD8033	Approved
0.6603	Remote Similarity	NPD8378	Approved
0.6603	Remote Similarity	NPD8380	Approved
0.6603	Remote Similarity	NPD8335	Approved
0.6603	Remote Similarity	NPD8296	Approved
0.6603	Remote Similarity	NPD8379	Approved
0.6601	Remote Similarity	NPD2629	Approved
0.6599	Remote Similarity	NPD6823	Phase 2
0.6595	Remote Similarity	NPD7472	Approved
0.6582	Remote Similarity	NPD6777	Approved
0.6582	Remote Similarity	NPD6781	Approved
0.6582	Remote Similarity	NPD6776	Approved
0.6582	Remote Similarity	NPD6782	Approved
0.6582	Remote Similarity	NPD6780	Approved
0.6582	Remote Similarity	NPD6779	Approved
0.6582	Remote Similarity	NPD6778	Approved
0.6579	Remote Similarity	NPD6858	Approved
0.6579	Remote Similarity	NPD7094	Approved
0.6578	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7808	Phase 3
0.6573	Remote Similarity	NPD5402	Approved
0.6573	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7698	Approved
0.6566	Remote Similarity	NPD7680	Approved
0.6566	Remote Similarity	NPD7696	Phase 3
0.6566	Remote Similarity	NPD7697	Approved
0.6558	Remote Similarity	NPD4198	Discontinued
0.655	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5736	Approved
0.6538	Remote Similarity	NPD6232	Discontinued
0.6538	Remote Similarity	NPD8294	Approved
0.6538	Remote Similarity	NPD8377	Approved
0.6536	Remote Similarity	NPD7768	Phase 2
0.6533	Remote Similarity	NPD7871	Phase 2
0.6533	Remote Similarity	NPD7870	Phase 2
0.6531	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD7097	Phase 1
0.6524	Remote Similarity	NPD7251	Discontinued
0.6517	Remote Similarity	NPD7701	Phase 2
0.651	Remote Similarity	NPD6685	Approved
0.6506	Remote Similarity	NPD6355	Discontinued
0.6502	Remote Similarity	NPD7801	Approved
0.6497	Remote Similarity	NPD7503	Approved
0.6497	Remote Similarity	NPD7411	Suspended
0.6494	Remote Similarity	NPD5951	Approved
0.6485	Remote Similarity	NPD8151	Discontinued
0.6474	Remote Similarity	NPD7610	Discontinued
0.6471	Remote Similarity	NPD6797	Phase 2
0.6467	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6166	Phase 2
0.6461	Remote Similarity	NPD6801	Discontinued
0.646	Remote Similarity	NPD7736	Approved
0.6457	Remote Similarity	NPD5403	Approved
0.6443	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD6212	Phase 3
0.6443	Remote Similarity	NPD6213	Phase 3
0.6437	Remote Similarity	NPD5401	Approved
0.6433	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6674	Discontinued
0.6425	Remote Similarity	NPD8404	Phase 2
0.6425	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD2182	Approved
0.6422	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7783	Phase 2
0.6418	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD2346	Discontinued
0.6407	Remote Similarity	NPD5735	Approved
0.64	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD3750	Approved
0.6395	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7003	Approved
0.6389	Remote Similarity	NPD3817	Phase 2
0.6384	Remote Similarity	NPD3226	Approved
0.638	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.638	Remote Similarity	NPD6085	Phase 2
0.6378	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6653	Approved
0.6369	Remote Similarity	NPD1934	Approved
0.6353	Remote Similarity	NPD5405	Approved
0.6353	Remote Similarity	NPD5408	Approved
0.6353	Remote Similarity	NPD5406	Approved
0.6353	Remote Similarity	NPD2935	Discontinued
0.6353	Remote Similarity	NPD7137	Phase 2
0.6353	Remote Similarity	NPD5404	Approved
0.6352	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6599	Discontinued
0.6347	Remote Similarity	NPD4140	Approved
0.6343	Remote Similarity	NPD2534	Approved
0.6343	Remote Similarity	NPD2533	Approved
0.6343	Remote Similarity	NPD7422	Clinical (unspecified phase)

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