NPASS Compound

Structure

CID131862 OpenBabel06191715492D 45 50 0 0 1 0 0 0 0 0999 V2000 1.9804 -3.7543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4361 -0.7720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5036 -2.3635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7247 -1.8065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3333 -4.0965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6122 0.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1399 -2.3418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1040 -1.3707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4022 0.5554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3097 1.9236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0618 2.1995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1524 -3.2907 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8389 -1.5160 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4910 -3.3124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1274 -2.5504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9554 -1.8566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4497 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4188 -0.3906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7612 1.6084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5700 1.0358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8981 1.6913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9378 -0.8979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1065 -0.4301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5977 -0.8792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6656 0.9831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7488 0.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9112 1.0042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7541 -0.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0949 0.5184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6000 -1.8337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0961 0.6518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7837 -2.3195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3065 -3.7976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4731 -3.4396 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1794 -0.8142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0260 2.1475 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3606 -2.2574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6939 1.1867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7966 -3.2683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9107 -0.2842 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5569 1.7229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3747 2.1864 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3369 -3.7759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1845 -2.4052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 40 1 0 0 0 0 6 41 1 0 0 0 0 7 12 1 0 0 0 0 7 16 1 0 0 0 0 8 13 1 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 9 20 1 0 0 0 0 10 19 2 0 0 0 0 10 21 1 0 0 0 0 11 42 1 0 0 0 0 11 43 1 0 0 0 0 12 1 1 1 0 0 0 12 44 1 0 0 0 0 13 2 1 6 0 0 0 13 45 1 0 0 0 0 14 34 2 0 0 0 0 14 44 1 0 0 0 0 15 35 2 0 0 0 0 15 45 1 0 0 0 0 16 22 1 0 0 0 0 16 32 2 0 0 0 0 17 23 1 0 0 0 0 17 33 2 0 0 0 0 18 24 1 0 0 0 0 18 36 1 0 0 0 0 19 25 1 0 0 0 0 19 37 1 0 0 0 0 20 26 2 0 0 0 0 20 42 1 0 0 0 0 21 27 2 0 0 0 0 21 43 1 0 0 0 0 22 23 2 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 24 28 2 0 0 0 0 24 30 1 0 0 0 0 25 29 2 0 0 0 0 25 31 1 0 0 0 0 26 27 1 0 0 0 0 26 28 1 0 0 0 0 27 29 1 0 0 0 0 30 32 1 0 0 0 0 30 38 2 0 0 0 0 31 33 1 0 0 0 0 31 39 2 0 0 0 0 32 40 1 0 0 0 0 33 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	618.17
Volume:	599.194
LogP:	6.019
LogD:	2.584
LogS:	-7.873
# Rotatable Bonds:	10
TPSA:	164.12
# H-Bond Aceptor:	12
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.146
Synthetic Accessibility Score:	4.471
Fsp3:	0.333
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:	-4.962
MDCK Permeability:	2.5183129764627665e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	80.6259994506836%
Volume Distribution (VD):	0.974
Pgp-substrate:	15.965139389038086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.317
CYP1A2-substrate:	0.237
CYP2C19-inhibitor:	0.59
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.913
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.172
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.106
CYP3A4-substrate:	0.06

ADMET: Excretion

Clearance (CL):	1.288
Half-life (T1/2):	0.172

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.583
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.315
Rat Oral Acute Toxicity:	0.109
Maximum Recommended Daily Dose:	0.497
Skin Sensitization:	0.789
Carcinogencity:	0.894
Eye Corrosion:	0.004
Eye Irritation:	0.373
Respiratory Toxicity:	0.037

Download Data

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

Natural Product: NPC131862

Natural Product ID:	NPC131862
*Common Name:**	AAWYBWDUDOICBF-CHWSQXEVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AAWYBWDUDOICBF-CHWSQXEVSA-N
Standard InCHI:	InChI=1S/C33H30O12/c1-12(44-14(3)34)7-16-22-23-17(8-13(2)45-15(4)35)33(41-6)31(39)25-19(37)10-21-27(29(23)25)26-20(42-11-43-21)9-18(36)24(28(22)26)30(38)32(16)40-5/h9-10,12-13,36-37H,7-8,11H2,1-6H3/t12-,13-/m1/s1
SMILES:	COC1=C(C[C@H](OC(=O)C)C)c2c3C(=C(OC)C(=O)c4c3c3c5c2c(C1=O)c(O)cc5OCOc3cc4O)C[C@H](OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047184
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002903] Perylenequinones

*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
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20550123]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22530813]
NPO21116	Aconitum soongaricum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[27328130]
NPO21116	Aconitum soongaricum	Species	Ranunculaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[27328130]
NPO21116	Aconitum soongaricum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21116	Aconitum soongaricum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27496	Streptomyces lividoclavatus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21116	Aconitum soongaricum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22073	Picea rubra	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23341	Arbutus unedo	Species	Ericaceae	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	9
Others	3

Activity Type	# Activity
Cell Line	5
Organism	4
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	4530.0	nM	PMID[502803]
NPT916	Cell Line	SK-MEL	Homo sapiens	IC50	=	4900.0	nM	PMID[502803]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	8700.0	nM	PMID[502803]
NPT457	Cell Line	BT-549	Homo sapiens	IC50	=	8700.0	nM	PMID[502803]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	4800.0	nM	PMID[502803]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2750.0	nM	PMID[502803]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1940.0	nM	PMID[502803]
NPT2	Others	Unspecified		Ratio IC50	=	1.6	n.a.	PMID[502803]
NPT2	Others	Unspecified		Ratio IC50	=	2.3	n.a.	PMID[502803]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	3100.0	nM	PMID[502803]
NPT27	Others	Unspecified		IC50	=	9400.0	nM	PMID[502803]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	9700.0	nM	PMID[502803]

☑ 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 NPC131862 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	403
0.1-0.2	1803
0.2-0.3	3882
0.3-0.4	9302
0.4-0.5	9256
0.5-0.6	4412
0.6-0.7	5828
0.7-0.8	6624
0.8-0.85	1083
0.85-0.9	91
0.9-0.95	9
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC229051
0.9691	High Similarity	NPC264063
0.9691	High Similarity	NPC469486
0.9198	High Similarity	NPC228654
0.9167	High Similarity	NPC470336
0.9167	High Similarity	NPC470335
0.9085	High Similarity	NPC219686
0.8895	High Similarity	NPC470334
0.8851	High Similarity	NPC470332
0.8824	High Similarity	NPC298778
0.8772	High Similarity	NPC477836
0.8757	High Similarity	NPC477835
0.8743	High Similarity	NPC475662
0.8743	High Similarity	NPC293227
0.8743	High Similarity	NPC473717
0.8743	High Similarity	NPC473631
0.8708	High Similarity	NPC314672
0.8706	High Similarity	NPC234497
0.8706	High Similarity	NPC105414
0.8706	High Similarity	NPC324522
0.8706	High Similarity	NPC472058
0.8706	High Similarity	NPC470341
0.8698	High Similarity	NPC469664
0.869	High Similarity	NPC15374
0.8678	High Similarity	NPC477682
0.8678	High Similarity	NPC477683
0.8671	High Similarity	NPC474345
0.8671	High Similarity	NPC68381
0.8671	High Similarity	NPC63105
0.8659	High Similarity	NPC48474
0.8655	High Similarity	NPC470206
0.8655	High Similarity	NPC259905
0.8655	High Similarity	NPC470207
0.8647	High Similarity	NPC178851
0.8644	High Similarity	NPC475220
0.8644	High Similarity	NPC475352
0.8644	High Similarity	NPC473686
0.8644	High Similarity	NPC221140
0.8644	High Similarity	NPC229817
0.8631	High Similarity	NPC472261
0.8631	High Similarity	NPC273467
0.8631	High Similarity	NPC189552
0.8629	High Similarity	NPC299149
0.8629	High Similarity	NPC153578
0.8629	High Similarity	NPC277710
0.8629	High Similarity	NPC114257
0.8619	High Similarity	NPC470195
0.8619	High Similarity	NPC470196
0.8619	High Similarity	NPC470193
0.8619	High Similarity	NPC470200
0.8619	High Similarity	NPC470194
0.8619	High Similarity	NPC470197
0.8619	High Similarity	NPC316274
0.8619	High Similarity	NPC282474
0.8619	High Similarity	NPC470198
0.8614	High Similarity	NPC146211
0.8613	High Similarity	NPC213052
0.8613	High Similarity	NPC470333
0.8613	High Similarity	NPC472054
0.8605	High Similarity	NPC477573
0.8605	High Similarity	NPC477571
0.8605	High Similarity	NPC477572
0.8588	High Similarity	NPC472051
0.8588	High Similarity	NPC472057
0.858	High Similarity	NPC477860
0.858	High Similarity	NPC475161
0.858	High Similarity	NPC315221
0.858	High Similarity	NPC472059
0.8571	High Similarity	NPC312993
0.8571	High Similarity	NPC472060
0.8571	High Similarity	NPC472052
0.8571	High Similarity	NPC186325
0.8571	High Similarity	NPC470342
0.8563	High Similarity	NPC474637
0.8563	High Similarity	NPC470454
0.8563	High Similarity	NPC470667
0.8563	High Similarity	NPC199533
0.8555	High Similarity	NPC271385
0.8555	High Similarity	NPC30432
0.8555	High Similarity	NPC5029
0.8555	High Similarity	NPC473113
0.8555	High Similarity	NPC111536
0.8555	High Similarity	NPC76128
0.8547	High Similarity	NPC473095
0.8547	High Similarity	NPC473096
0.8539	High Similarity	NPC87583
0.8538	High Similarity	NPC30027
0.8531	High Similarity	NPC313452
0.8529	High Similarity	NPC472053
0.8529	High Similarity	NPC290160
0.8523	High Similarity	NPC70318
0.8523	High Similarity	NPC84494
0.8523	High Similarity	NPC245059
0.8521	High Similarity	NPC18380
0.8514	High Similarity	NPC475246
0.8514	High Similarity	NPC46958
0.8512	High Similarity	NPC324736
0.8512	High Similarity	NPC177650
0.8508	High Similarity	NPC470199
0.8508	High Similarity	NPC314459
0.8497	Intermediate Similarity	NPC193698
0.8492	Intermediate Similarity	NPC105591
0.8488	Intermediate Similarity	NPC473094
0.8488	Intermediate Similarity	NPC76647
0.8485	Intermediate Similarity	NPC232645
0.8485	Intermediate Similarity	NPC72958
0.8485	Intermediate Similarity	NPC149526
0.8485	Intermediate Similarity	NPC474417
0.8483	Intermediate Similarity	NPC75574
0.848	Intermediate Similarity	NPC71390
0.8475	Intermediate Similarity	NPC470453
0.8475	Intermediate Similarity	NPC164047
0.8475	Intermediate Similarity	NPC470448
0.8475	Intermediate Similarity	NPC470452
0.8466	Intermediate Similarity	NPC34802
0.8462	Intermediate Similarity	NPC292863
0.8462	Intermediate Similarity	NPC184326
0.8457	Intermediate Similarity	NPC98667
0.8457	Intermediate Similarity	NPC86809
0.8457	Intermediate Similarity	NPC186800
0.8457	Intermediate Similarity	NPC477992
0.8457	Intermediate Similarity	NPC3718
0.8457	Intermediate Similarity	NPC232412
0.8457	Intermediate Similarity	NPC477991
0.8452	Intermediate Similarity	NPC246466
0.8452	Intermediate Similarity	NPC263483
0.8444	Intermediate Similarity	NPC205721
0.8443	Intermediate Similarity	NPC66508
0.8443	Intermediate Similarity	NPC226656
0.8436	Intermediate Similarity	NPC197972
0.8436	Intermediate Similarity	NPC241847
0.8434	Intermediate Similarity	NPC87708
0.8434	Intermediate Similarity	NPC273483
0.8434	Intermediate Similarity	NPC217447
0.8434	Intermediate Similarity	NPC175978
0.8424	Intermediate Similarity	NPC477914
0.8424	Intermediate Similarity	NPC475460
0.8424	Intermediate Similarity	NPC470568
0.8424	Intermediate Similarity	NPC325983
0.8424	Intermediate Similarity	NPC119929
0.8415	Intermediate Similarity	NPC472841
0.8412	Intermediate Similarity	NPC175513
0.8412	Intermediate Similarity	NPC117985
0.8412	Intermediate Similarity	NPC137232
0.8409	Intermediate Similarity	NPC469345
0.8409	Intermediate Similarity	NPC475233
0.8405	Intermediate Similarity	NPC163846
0.8405	Intermediate Similarity	NPC225173
0.8402	Intermediate Similarity	NPC55443
0.8402	Intermediate Similarity	NPC18699
0.8402	Intermediate Similarity	NPC195167
0.8402	Intermediate Similarity	NPC474373
0.8402	Intermediate Similarity	NPC51760
0.84	Intermediate Similarity	NPC85368
0.84	Intermediate Similarity	NPC154986
0.84	Intermediate Similarity	NPC98776
0.8398	Intermediate Similarity	NPC201814
0.8393	Intermediate Similarity	NPC164244
0.8393	Intermediate Similarity	NPC474360
0.8391	Intermediate Similarity	NPC76047
0.8383	Intermediate Similarity	NPC329844
0.8382	Intermediate Similarity	NPC249977
0.8378	Intermediate Similarity	NPC131405
0.8373	Intermediate Similarity	NPC478148
0.8373	Intermediate Similarity	NPC133856
0.8373	Intermediate Similarity	NPC230848
0.8373	Intermediate Similarity	NPC470569
0.8372	Intermediate Similarity	NPC7752
0.8371	Intermediate Similarity	NPC208069
0.8371	Intermediate Similarity	NPC265795
0.8364	Intermediate Similarity	NPC288036
0.8364	Intermediate Similarity	NPC100985
0.8364	Intermediate Similarity	NPC65589
0.8364	Intermediate Similarity	NPC329933
0.8364	Intermediate Similarity	NPC97028
0.8364	Intermediate Similarity	NPC291049
0.8364	Intermediate Similarity	NPC158338
0.8364	Intermediate Similarity	NPC97029
0.8364	Intermediate Similarity	NPC233267
0.8363	Intermediate Similarity	NPC216752
0.8363	Intermediate Similarity	NPC473022
0.8362	Intermediate Similarity	NPC47191
0.8362	Intermediate Similarity	NPC5671
0.8362	Intermediate Similarity	NPC477895
0.8354	Intermediate Similarity	NPC125801
0.8353	Intermediate Similarity	NPC472055
0.8352	Intermediate Similarity	NPC321046
0.8352	Intermediate Similarity	NPC264302
0.8343	Intermediate Similarity	NPC478226
0.8343	Intermediate Similarity	NPC91650
0.8333	Intermediate Similarity	NPC5319
0.8333	Intermediate Similarity	NPC297195
0.8333	Intermediate Similarity	NPC207574
0.8333	Intermediate Similarity	NPC222455
0.8333	Intermediate Similarity	NPC89625
0.8333	Intermediate Similarity	NPC473202
0.8333	Intermediate Similarity	NPC54903
0.8333	Intermediate Similarity	NPC286074
0.8333	Intermediate Similarity	NPC149618
0.8333	Intermediate Similarity	NPC84266

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 NPC131862 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	1036
0.2-0.3	1900
0.3-0.4	2663
0.4-0.5	1875
0.5-0.6	872
0.6-0.7	286
0.7-0.8	135
0.8-0.85	22
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8743	High Similarity	NPD6959	Discontinued
0.8492	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD7473	Discontinued
0.8278	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7819	Suspended
0.8161	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7075	Discontinued
0.8121	Intermediate Similarity	NPD2533	Approved
0.8121	Intermediate Similarity	NPD2532	Approved
0.8121	Intermediate Similarity	NPD2534	Approved
0.8118	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD6559	Discontinued
0.8061	Intermediate Similarity	NPD7390	Discontinued
0.8047	Intermediate Similarity	NPD7411	Suspended
0.8045	Intermediate Similarity	NPD7808	Phase 3
0.8034	Intermediate Similarity	NPD6797	Phase 2
0.8023	Intermediate Similarity	NPD5844	Phase 1
0.8021	Intermediate Similarity	NPD8151	Discontinued
0.8012	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD8312	Approved
0.8	Intermediate Similarity	NPD8313	Approved
0.7989	Intermediate Similarity	NPD7251	Discontinued
0.7965	Intermediate Similarity	NPD7768	Phase 2
0.7955	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD6166	Phase 2
0.7955	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD7435	Discontinued
0.7944	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD4380	Phase 2
0.7877	Intermediate Similarity	NPD7074	Phase 3
0.7866	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7054	Approved
0.7812	Intermediate Similarity	NPD7870	Phase 2
0.7812	Intermediate Similarity	NPD7871	Phase 2
0.7803	Intermediate Similarity	NPD3817	Phase 2
0.7798	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD7874	Approved
0.7789	Intermediate Similarity	NPD6777	Approved
0.7789	Intermediate Similarity	NPD6776	Approved
0.7789	Intermediate Similarity	NPD6780	Approved
0.7789	Intermediate Similarity	NPD6781	Approved
0.7789	Intermediate Similarity	NPD6782	Approved
0.7789	Intermediate Similarity	NPD6779	Approved
0.7789	Intermediate Similarity	NPD6778	Approved
0.7778	Intermediate Similarity	NPD7472	Approved
0.7778	Intermediate Similarity	NPD6599	Discontinued
0.7772	Intermediate Similarity	NPD8150	Discontinued
0.776	Intermediate Similarity	NPD7697	Approved
0.776	Intermediate Similarity	NPD7696	Phase 3
0.776	Intermediate Similarity	NPD7698	Approved
0.7759	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD3226	Approved
0.7714	Intermediate Similarity	NPD3749	Approved
0.7688	Intermediate Similarity	NPD37	Approved
0.767	Intermediate Similarity	NPD6234	Discontinued
0.7667	Intermediate Similarity	NPD3818	Discontinued
0.7667	Intermediate Similarity	NPD3751	Discontinued
0.7665	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7783	Phase 2
0.7665	Intermediate Similarity	NPD3750	Approved
0.7657	Intermediate Similarity	NPD4965	Approved
0.7657	Intermediate Similarity	NPD4967	Phase 2
0.7657	Intermediate Similarity	NPD4966	Approved
0.7633	Intermediate Similarity	NPD6799	Approved
0.7629	Intermediate Similarity	NPD8320	Phase 1
0.7629	Intermediate Similarity	NPD8319	Approved
0.7622	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7458	Discontinued
0.7602	Intermediate Similarity	NPD7701	Phase 2
0.76	Intermediate Similarity	NPD5402	Approved
0.7598	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1934	Approved
0.7576	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1510	Phase 2
0.7569	Intermediate Similarity	NPD7228	Approved
0.7561	Intermediate Similarity	NPD1607	Approved
0.7545	Intermediate Similarity	NPD1549	Phase 2
0.7542	Intermediate Similarity	NPD3787	Discontinued
0.7542	Intermediate Similarity	NPD5710	Approved
0.7542	Intermediate Similarity	NPD5711	Approved
0.753	Intermediate Similarity	NPD2935	Discontinued
0.753	Intermediate Similarity	NPD5406	Approved
0.753	Intermediate Similarity	NPD5408	Approved
0.753	Intermediate Similarity	NPD5405	Approved
0.753	Intermediate Similarity	NPD5404	Approved
0.7526	Intermediate Similarity	NPD6534	Approved
0.7526	Intermediate Similarity	NPD6535	Approved
0.7514	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7699	Phase 2
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD7700	Phase 2
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7801	Approved
0.7458	Intermediate Similarity	NPD3882	Suspended
0.7456	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7003	Approved
0.7443	Intermediate Similarity	NPD1465	Phase 2
0.7443	Intermediate Similarity	NPD8455	Phase 2
0.7442	Intermediate Similarity	NPD1512	Approved
0.7439	Intermediate Similarity	NPD1240	Approved
0.7425	Intermediate Similarity	NPD2796	Approved
0.7396	Intermediate Similarity	NPD2800	Approved
0.7389	Intermediate Similarity	NPD7199	Phase 2
0.7384	Intermediate Similarity	NPD5401	Approved
0.7384	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2346	Discontinued
0.7365	Intermediate Similarity	NPD3748	Approved
0.7358	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6651	Approved
0.7347	Intermediate Similarity	NPD6823	Phase 2
0.7345	Intermediate Similarity	NPD2801	Approved
0.7333	Intermediate Similarity	NPD5494	Approved
0.7326	Intermediate Similarity	NPD1511	Approved
0.7321	Intermediate Similarity	NPD1551	Phase 2
0.7299	Intermediate Similarity	NPD920	Approved
0.7278	Intermediate Similarity	NPD919	Approved
0.7262	Intermediate Similarity	NPD2799	Discontinued
0.7253	Intermediate Similarity	NPD7229	Phase 3
0.7251	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7240	Approved
0.7193	Intermediate Similarity	NPD1243	Approved
0.7189	Intermediate Similarity	NPD7177	Discontinued
0.7184	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD5953	Discontinued
0.7151	Intermediate Similarity	NPD7286	Phase 2
0.7151	Intermediate Similarity	NPD4628	Phase 3
0.715	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD8434	Phase 2
0.7118	Intermediate Similarity	NPD6100	Approved
0.7118	Intermediate Similarity	NPD6099	Approved
0.7113	Intermediate Similarity	NPD6213	Phase 3
0.7113	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6212	Phase 3
0.7108	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8067	Phase 3
0.7027	Intermediate Similarity	NPD3926	Phase 2
0.7011	Intermediate Similarity	NPD1247	Approved
0.7006	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7799	Discontinued
0.7	Intermediate Similarity	NPD8366	Approved
0.6957	Remote Similarity	NPD7930	Approved
0.6951	Remote Similarity	NPD1283	Approved
0.6949	Remote Similarity	NPD6273	Approved
0.6947	Remote Similarity	NPD7685	Pre-registration
0.6946	Remote Similarity	NPD4625	Phase 3
0.6923	Remote Similarity	NPD4060	Phase 1
0.6923	Remote Similarity	NPD2979	Phase 3
0.6919	Remote Similarity	NPD2438	Suspended
0.6915	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6190	Approved
0.6911	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2313	Discontinued
0.6905	Remote Similarity	NPD3764	Approved
0.6905	Remote Similarity	NPD6798	Discontinued
0.6902	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4908	Phase 1
0.6882	Remote Similarity	NPD230	Phase 1
0.6881	Remote Similarity	NPD7680	Approved
0.6879	Remote Similarity	NPD2344	Approved
0.6872	Remote Similarity	NPD4287	Approved
0.6871	Remote Similarity	NPD1201	Approved
0.6869	Remote Similarity	NPD8491	Approved
0.6867	Remote Similarity	NPD2798	Approved
0.6865	Remote Similarity	NPD6746	Phase 2
0.6863	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7584	Approved
0.686	Remote Similarity	NPD651	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.685	Remote Similarity	NPD8285	Discontinued
0.6837	Remote Similarity	NPD8059	Phase 3
0.6837	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD8469	Approved
0.6831	Remote Similarity	NPD4288	Approved
0.6818	Remote Similarity	NPD4360	Phase 2
0.6818	Remote Similarity	NPD4363	Phase 3
0.6809	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1470	Approved
0.6786	Remote Similarity	NPD6832	Phase 2
0.6776	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1281	Approved
0.6765	Remote Similarity	NPD6233	Phase 2
0.6763	Remote Similarity	NPD7033	Discontinued
0.6761	Remote Similarity	NPD8166	Discontinued
0.6758	Remote Similarity	NPD7615	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