NPASS Compound

Structure

NPC476229 OpenBabel07101718302D 48 53 0 0 1 0 0 0 0 0999 V2000 3.9690 -1.2666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4690 -2.1326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3876 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3445 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8030 3.2574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5855 -2.1908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6719 -2.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4690 -0.4006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6392 -1.9588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9690 0.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4690 -0.4006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5216 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3876 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2052 1.6318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7752 -1.6023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9690 0.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4690 -1.2017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4370 0.9916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3876 -1.6023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4864 -1.6073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9690 -1.2666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5216 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0349 2.6172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0814 -1.2017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6938 -1.2017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7983 -1.3951 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6938 -1.2017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3876 -1.6023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0814 -0.4006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6938 -0.4006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0963 2.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1352 -0.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7765 -1.6030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4690 -0.4006 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0814 -1.2017 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6073 0.0062 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6938 -0.4006 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3876 -2.6023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.6023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9260 3.9477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3281 2.3221 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0661 -0.1183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0789 -1.1305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7752 -0.0000 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 -2.2765 -0.7370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 35 1 0 0 0 0 7 35 1 0 0 0 0 9 45 1 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 21 2 0 0 0 0 12 13 1 0 0 0 0 12 22 2 0 0 0 0 13 25 1 0 0 0 0 14 18 1 0 0 0 0 14 23 2 0 0 0 0 15 17 2 0 0 0 0 15 24 1 0 0 0 0 16 36 1 0 0 0 0 17 36 1 0 0 0 0 18 38 1 0 0 0 0 19 26 2 0 0 0 0 19 37 1 0 0 0 0 20 27 1 0 0 0 0 20 37 1 0 0 0 0 23 33 1 0 0 0 0 24 29 2 0 0 0 0 24 31 1 0 0 0 0 25 31 2 0 0 0 0 25 32 1 0 0 0 0 26 30 1 0 0 0 0 27 35 1 0 0 0 0 27 39 1 1 0 0 0 28 29 1 0 0 0 0 28 30 1 0 0 0 0 28 32 2 0 0 0 0 29 40 1 0 0 0 0 30 41 2 0 0 0 0 31 46 1 0 0 0 0 32 47 1 0 0 0 0 33 42 2 0 0 0 0 33 43 1 0 0 0 0 34 37 1 0 0 0 0 34 38 1 0 0 0 0 34 44 2 0 0 0 0 35 48 1 0 0 0 0 36 8 1 1 0 0 0 36 46 1 0 0 0 0 37 45 1 6 0 0 0 38 39 1 1 0 0 0 38 48 1 0 0 0 0 39 26 1 1 0 0 0 39 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	658.31
Volume:	681.872
LogP:	7.97
LogD:	3.959
LogS:	-3.243
# Rotatable Bonds:	9
TPSA:	128.59
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.273
Synthetic Accessibility Score:	7.116
Fsp3:	0.513
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:	-4.966
MDCK Permeability:	1.8591004845802672e-05
Pgp-inhibitor:	0.785
Pgp-substrate:	0.938
Human Intestinal Absorption (HIA):	0.394
20% Bioavailability (F20%):	0.583
30% Bioavailability (F30%):	0.8

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.431
Plasma Protein Binding (PPB):	88.38533782958984%
Volume Distribution (VD):	1.33
Pgp-substrate:	9.003443717956543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.6
CYP2C9-inhibitor:	0.347
CYP2C9-substrate:	0.096
CYP2D6-inhibitor:	0.256
CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.697
CYP3A4-substrate:	0.931

ADMET: Excretion

Clearance (CL):	4.775
Half-life (T1/2):	0.034

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.978
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.111
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.852
Skin Sensitization:	0.28
Carcinogencity:	0.946
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC476229

Natural Product ID:	NPC476229
*Common Name:**	VFBTVWAAPNXXAP-NVRXUDDSSA-N
IUPAC Name:	n.a.
Synonyms:	7-Methoxygambogic Acid
Standard InCHIKey:	VFBTVWAAPNXXAP-NVRXUDDSSA-N
Standard InCHI:	InChI=1S/C39H46O9/c1-21(2)11-10-16-36(8)17-15-24-29(40)28-30(41)26-19-37(45-9)20-27-35(6,7)48-38(34(37)44,18-14-23(5)33(42)43)39(26,27)47-32(28)25(31(24)46-36)13-12-22(3)4/h11-12,14-15,17,19,27,40H,10,13,16,18,20H2,1-9H3,(H,42,43)/b23-14-/t27-,36+,37+,38-,39+/m0/s1
SMILES:	CO[C@]12C=C3C(=O)c4c(O[C@]53[C@@H](C1)C(O[C@]5(C2=O)C/C=C(C(=O)O)/C)(C)C)c(CC=C(C)C)c1c(c4O)C=C[C@@](O1)(C)CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL556736
PubChem CID:	45268014
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003521] Pyranoxanthones

*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
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	latex	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	resin	n.a.	n.a.	PMID[19072548]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21486005]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	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
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	930.0	nM	PMID[488687]

☑ 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 NPC476229 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	398
0.1-0.2	1548
0.2-0.3	3212
0.3-0.4	6842
0.4-0.5	10636
0.5-0.6	6435
0.6-0.7	5869
0.7-0.8	7378
0.8-0.85	301
0.85-0.9	27
0.9-0.95	29
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC476152
0.9814	High Similarity	NPC47634
0.9814	High Similarity	NPC75141
0.9814	High Similarity	NPC55422
0.9755	High Similarity	NPC476139
0.9693	High Similarity	NPC476159
0.9691	High Similarity	NPC40089
0.9691	High Similarity	NPC158329
0.9691	High Similarity	NPC476146
0.9632	High Similarity	NPC476196
0.9627	High Similarity	NPC189689
0.9578	High Similarity	NPC476199
0.9578	High Similarity	NPC476210
0.9571	High Similarity	NPC476216
0.9565	High Similarity	NPC131578
0.9509	High Similarity	NPC223413
0.9461	High Similarity	NPC233978
0.9451	High Similarity	NPC41598
0.9398	High Similarity	NPC476311
0.9379	High Similarity	NPC286422
0.9341	High Similarity	NPC162248
0.9329	High Similarity	NPC62444
0.929	High Similarity	NPC473607
0.9286	High Similarity	NPC227275
0.9222	High Similarity	NPC169018
0.9217	High Similarity	NPC63514
0.9212	High Similarity	NPC476255
0.9207	High Similarity	NPC476931
0.9176	High Similarity	NPC473729
0.9172	High Similarity	NPC98943
0.9157	High Similarity	NPC193222
0.9146	High Similarity	NPC94796
0.9102	High Similarity	NPC102810
0.9096	High Similarity	NPC476056
0.9024	High Similarity	NPC475107
0.9024	High Similarity	NPC43490
0.9	High Similarity	NPC475398
0.8944	High Similarity	NPC476162
0.8941	High Similarity	NPC475080
0.8902	High Similarity	NPC476930
0.8882	High Similarity	NPC118128
0.8855	High Similarity	NPC476929
0.881	High Similarity	NPC473908
0.8728	High Similarity	NPC469345
0.869	High Similarity	NPC475106
0.8671	High Similarity	NPC232412
0.8671	High Similarity	NPC86809
0.8671	High Similarity	NPC98667
0.8663	High Similarity	NPC477529
0.8655	High Similarity	NPC207574
0.8655	High Similarity	NPC297195
0.8655	High Similarity	NPC291795
0.8647	High Similarity	NPC475109
0.8623	High Similarity	NPC125969
0.8613	High Similarity	NPC469393
0.8613	High Similarity	NPC17105
0.8613	High Similarity	NPC73899
0.8613	High Similarity	NPC474276
0.8613	High Similarity	NPC147363
0.8605	High Similarity	NPC241387
0.8605	High Similarity	NPC193698
0.8605	High Similarity	NPC251144
0.8596	High Similarity	NPC174486
0.8571	High Similarity	NPC243701
0.8563	High Similarity	NPC294149
0.8547	High Similarity	NPC54903
0.8547	High Similarity	NPC286074
0.8531	High Similarity	NPC475148
0.8531	High Similarity	NPC475656
0.8521	High Similarity	NPC103816
0.8521	High Similarity	NPC61382
0.8488	Intermediate Similarity	NPC292233
0.8483	Intermediate Similarity	NPC106700
0.8475	Intermediate Similarity	NPC208069
0.8466	Intermediate Similarity	NPC477682
0.8466	Intermediate Similarity	NPC477683
0.8462	Intermediate Similarity	NPC172687
0.8448	Intermediate Similarity	NPC472620
0.8443	Intermediate Similarity	NPC469934
0.8436	Intermediate Similarity	NPC197972
0.843	Intermediate Similarity	NPC120857
0.843	Intermediate Similarity	NPC85047
0.843	Intermediate Similarity	NPC323137
0.843	Intermediate Similarity	NPC469394
0.843	Intermediate Similarity	NPC17274
0.8424	Intermediate Similarity	NPC321387
0.8424	Intermediate Similarity	NPC327059
0.8421	Intermediate Similarity	NPC469395
0.8402	Intermediate Similarity	NPC311574
0.8402	Intermediate Similarity	NPC264932
0.84	Intermediate Similarity	NPC470942
0.8398	Intermediate Similarity	NPC295436
0.8389	Intermediate Similarity	NPC294863
0.8389	Intermediate Similarity	NPC282636
0.8382	Intermediate Similarity	NPC76647
0.8362	Intermediate Similarity	NPC5671
0.8361	Intermediate Similarity	NPC314020
0.8352	Intermediate Similarity	NPC245975
0.8343	Intermediate Similarity	NPC161650
0.8343	Intermediate Similarity	NPC210048
0.8343	Intermediate Similarity	NPC473113
0.8333	Intermediate Similarity	NPC473096
0.8333	Intermediate Similarity	NPC476169
0.8333	Intermediate Similarity	NPC471456
0.8333	Intermediate Similarity	NPC472619
0.8333	Intermediate Similarity	NPC473095
0.8333	Intermediate Similarity	NPC20734
0.8324	Intermediate Similarity	NPC182693
0.8323	Intermediate Similarity	NPC288534
0.8315	Intermediate Similarity	NPC244903
0.8313	Intermediate Similarity	NPC180351
0.8313	Intermediate Similarity	NPC476509
0.8313	Intermediate Similarity	NPC470908
0.8305	Intermediate Similarity	NPC312630
0.8305	Intermediate Similarity	NPC324220
0.8304	Intermediate Similarity	NPC92589
0.8304	Intermediate Similarity	NPC472346
0.8304	Intermediate Similarity	NPC117985
0.8303	Intermediate Similarity	NPC211811
0.8303	Intermediate Similarity	NPC472345
0.8297	Intermediate Similarity	NPC314672
0.8295	Intermediate Similarity	NPC154986
0.8294	Intermediate Similarity	NPC474373
0.8293	Intermediate Similarity	NPC82534
0.8286	Intermediate Similarity	NPC315306
0.8286	Intermediate Similarity	NPC101107
0.8286	Intermediate Similarity	NPC313717
0.8284	Intermediate Similarity	NPC475797
0.8284	Intermediate Similarity	NPC474738
0.8284	Intermediate Similarity	NPC78554
0.8284	Intermediate Similarity	NPC129053
0.8284	Intermediate Similarity	NPC469936
0.8284	Intermediate Similarity	NPC321372
0.8284	Intermediate Similarity	NPC474609
0.8284	Intermediate Similarity	NPC164427
0.8284	Intermediate Similarity	NPC470354
0.8284	Intermediate Similarity	NPC109967
0.8284	Intermediate Similarity	NPC470352
0.828	Intermediate Similarity	NPC131405
0.8276	Intermediate Similarity	NPC478059
0.8276	Intermediate Similarity	NPC473094
0.8276	Intermediate Similarity	NPC283041
0.8276	Intermediate Similarity	NPC478060
0.8276	Intermediate Similarity	NPC471975
0.8276	Intermediate Similarity	NPC470374
0.8276	Intermediate Similarity	NPC470377
0.8276	Intermediate Similarity	NPC126204
0.8274	Intermediate Similarity	NPC209760
0.8274	Intermediate Similarity	NPC477669
0.8274	Intermediate Similarity	NPC192189
0.8274	Intermediate Similarity	NPC100134
0.8274	Intermediate Similarity	NPC311579
0.8274	Intermediate Similarity	NPC471695
0.8274	Intermediate Similarity	NPC472799
0.8274	Intermediate Similarity	NPC236756
0.8268	Intermediate Similarity	NPC6709
0.8266	Intermediate Similarity	NPC294722
0.8266	Intermediate Similarity	NPC204088
0.8266	Intermediate Similarity	NPC329215
0.8266	Intermediate Similarity	NPC316262
0.8266	Intermediate Similarity	NPC314653
0.8266	Intermediate Similarity	NPC259007
0.8266	Intermediate Similarity	NPC191930
0.8258	Intermediate Similarity	NPC207467
0.8256	Intermediate Similarity	NPC229632
0.8256	Intermediate Similarity	NPC219861
0.8256	Intermediate Similarity	NPC472402
0.8256	Intermediate Similarity	NPC473022
0.8253	Intermediate Similarity	NPC198927
0.8251	Intermediate Similarity	NPC48474
0.8249	Intermediate Similarity	NPC289244
0.8242	Intermediate Similarity	NPC137296
0.8242	Intermediate Similarity	NPC474108
0.8242	Intermediate Similarity	NPC177995
0.8239	Intermediate Similarity	NPC475825
0.8239	Intermediate Similarity	NPC223375
0.8239	Intermediate Similarity	NPC121333
0.8239	Intermediate Similarity	NPC475669
0.8235	Intermediate Similarity	NPC201127
0.8235	Intermediate Similarity	NPC474637
0.8235	Intermediate Similarity	NPC472889
0.8235	Intermediate Similarity	NPC263483
0.8235	Intermediate Similarity	NPC246466
0.8232	Intermediate Similarity	NPC206212
0.8232	Intermediate Similarity	NPC71184
0.8229	Intermediate Similarity	NPC475805
0.8229	Intermediate Similarity	NPC242395
0.8229	Intermediate Similarity	NPC217378
0.8229	Intermediate Similarity	NPC177480
0.8229	Intermediate Similarity	NPC152477
0.8225	Intermediate Similarity	NPC108937
0.8225	Intermediate Similarity	NPC279218
0.8225	Intermediate Similarity	NPC478221
0.8225	Intermediate Similarity	NPC472890
0.8225	Intermediate Similarity	NPC317585
0.8225	Intermediate Similarity	NPC275575
0.8221	Intermediate Similarity	NPC472344
0.8218	Intermediate Similarity	NPC39091
0.8218	Intermediate Similarity	NPC20237
0.8218	Intermediate Similarity	NPC13481

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 NPC476229 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	934
0.2-0.3	1943
0.3-0.4	2642
0.4-0.5	1960
0.5-0.6	889
0.6-0.7	287
0.7-0.8	139
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8343	Intermediate Similarity	NPD7075	Discontinued
0.8166	Intermediate Similarity	NPD7819	Suspended
0.8166	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
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)
0.8057	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7411	Suspended
0.8012	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD6801	Discontinued
0.7989	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD8434	Phase 2
0.7931	Intermediate Similarity	NPD5494	Approved
0.7927	Intermediate Similarity	NPD2800	Approved
0.7907	Intermediate Similarity	NPD3817	Phase 2
0.7904	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD4380	Phase 2
0.7869	Intermediate Similarity	NPD8150	Discontinued
0.7861	Intermediate Similarity	NPD3882	Suspended
0.7845	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD7808	Phase 3
0.7841	Intermediate Similarity	NPD6232	Discontinued
0.7816	Intermediate Similarity	NPD3749	Approved
0.7803	Intermediate Similarity	NPD5402	Approved
0.779	Intermediate Similarity	NPD7251	Discontinued
0.7784	Intermediate Similarity	NPD1247	Approved
0.7778	Intermediate Similarity	NPD6599	Discontinued
0.7771	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6166	Phase 2
0.7753	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD2801	Approved
0.7738	Intermediate Similarity	NPD6799	Approved
0.7735	Intermediate Similarity	NPD6797	Phase 2
0.7722	Intermediate Similarity	NPD5844	Phase 1
0.7717	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6959	Discontinued
0.767	Intermediate Similarity	NPD919	Approved
0.7667	Intermediate Similarity	NPD3818	Discontinued
0.7665	Intermediate Similarity	NPD3750	Approved
0.7657	Intermediate Similarity	NPD7768	Phase 2
0.7657	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5711	Approved
0.764	Intermediate Similarity	NPD5710	Approved
0.7637	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD7054	Approved
0.7616	Intermediate Similarity	NPD3226	Approved
0.7602	Intermediate Similarity	NPD5403	Approved
0.7596	Intermediate Similarity	NPD6559	Discontinued
0.7594	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1934	Approved
0.7582	Intermediate Similarity	NPD7472	Approved
0.7582	Intermediate Similarity	NPD7074	Phase 3
0.7561	Intermediate Similarity	NPD6651	Approved
0.756	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD1512	Approved
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD920	Approved
0.7487	Intermediate Similarity	NPD7435	Discontinued
0.7485	Intermediate Similarity	NPD5401	Approved
0.7473	Intermediate Similarity	NPD3751	Discontinued
0.7459	Intermediate Similarity	NPD2403	Approved
0.7443	Intermediate Similarity	NPD1465	Phase 2
0.744	Intermediate Similarity	NPD1549	Phase 2
0.7427	Intermediate Similarity	NPD1511	Approved
0.7396	Intermediate Similarity	NPD1243	Approved
0.7396	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2346	Discontinued
0.7365	Intermediate Similarity	NPD3748	Approved
0.7365	Intermediate Similarity	NPD1510	Phase 2
0.7358	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7874	Approved
0.7321	Intermediate Similarity	NPD2796	Approved
0.7321	Intermediate Similarity	NPD2935	Discontinued
0.731	Intermediate Similarity	NPD7697	Approved
0.731	Intermediate Similarity	NPD7696	Phase 3
0.731	Intermediate Similarity	NPD7698	Approved
0.7308	Intermediate Similarity	NPD3926	Phase 2
0.7289	Intermediate Similarity	NPD5124	Phase 1
0.7289	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7871	Phase 2
0.7273	Intermediate Similarity	NPD7870	Phase 2
0.7267	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2799	Discontinued
0.7253	Intermediate Similarity	NPD3787	Discontinued
0.7246	Intermediate Similarity	NPD1607	Approved
0.7246	Intermediate Similarity	NPD8366	Approved
0.7245	Intermediate Similarity	NPD6776	Approved
0.7245	Intermediate Similarity	NPD6782	Approved
0.7245	Intermediate Similarity	NPD6780	Approved
0.7245	Intermediate Similarity	NPD6778	Approved
0.7245	Intermediate Similarity	NPD6777	Approved
0.7245	Intermediate Similarity	NPD6781	Approved
0.7245	Intermediate Similarity	NPD6779	Approved
0.7229	Intermediate Similarity	NPD1240	Approved
0.7219	Intermediate Similarity	NPD6099	Approved
0.7219	Intermediate Similarity	NPD6100	Approved
0.7214	Intermediate Similarity	NPD8151	Discontinued
0.7213	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2313	Discontinued
0.7194	Intermediate Similarity	NPD8285	Discontinued
0.7189	Intermediate Similarity	NPD7228	Approved
0.7186	Intermediate Similarity	NPD8319	Approved
0.7186	Intermediate Similarity	NPD8320	Phase 1
0.7166	Intermediate Similarity	NPD5953	Discontinued
0.7164	Intermediate Similarity	NPD7701	Phase 2
0.7157	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7286	Phase 2
0.7143	Intermediate Similarity	NPD7801	Approved
0.7143	Intermediate Similarity	NPD7783	Phase 2
0.7143	Intermediate Similarity	NPD7700	Phase 2
0.7143	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7699	Phase 2
0.7119	Intermediate Similarity	NPD7458	Discontinued
0.7118	Intermediate Similarity	NPD1551	Phase 2
0.7109	Intermediate Similarity	NPD8491	Approved
0.7102	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD37	Approved
0.709	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD6234	Discontinued
0.7081	Intermediate Similarity	NPD7907	Approved
0.7077	Intermediate Similarity	NPD6534	Approved
0.7077	Intermediate Similarity	NPD6535	Approved
0.7076	Intermediate Similarity	NPD1471	Phase 3
0.7075	Intermediate Similarity	NPD8469	Approved
0.7072	Intermediate Similarity	NPD4967	Phase 2
0.7072	Intermediate Similarity	NPD4966	Approved
0.7072	Intermediate Similarity	NPD4965	Approved
0.7065	Intermediate Similarity	NPD7229	Phase 3
0.7052	Intermediate Similarity	NPD4628	Phase 3
0.7047	Intermediate Similarity	NPD4287	Approved
0.7037	Intermediate Similarity	NPD7685	Pre-registration
0.7029	Intermediate Similarity	NPD7390	Discontinued
0.7011	Intermediate Similarity	NPD7199	Phase 2
0.7006	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3268	Approved
0.7005	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD447	Suspended
0.6977	Remote Similarity	NPD2344	Approved
0.6959	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6764	Approved
0.6947	Remote Similarity	NPD6765	Approved
0.6927	Remote Similarity	NPD8407	Phase 2
0.6927	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8127	Discontinued
0.6915	Remote Similarity	NPD7799	Discontinued
0.6915	Remote Similarity	NPD6823	Phase 2
0.6914	Remote Similarity	NPD6190	Approved
0.6905	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.689	Remote Similarity	NPD8404	Phase 2
0.6882	Remote Similarity	NPD230	Phase 1
0.6882	Remote Similarity	NPD6355	Discontinued
0.6879	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD8455	Phase 2
0.6868	Remote Similarity	NPD5761	Phase 2
0.6868	Remote Similarity	NPD5760	Phase 2
0.6863	Remote Similarity	NPD7584	Approved
0.686	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD8368	Discontinued
0.6859	Remote Similarity	NPD7240	Approved
0.6857	Remote Similarity	NPD7003	Approved
0.6854	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4288	Approved
0.6825	Remote Similarity	NPD4111	Phase 1
0.6825	Remote Similarity	NPD4665	Approved
0.6824	Remote Similarity	NPD4060	Phase 1
0.6821	Remote Similarity	NPD5406	Approved
0.6821	Remote Similarity	NPD5408	Approved
0.6821	Remote Similarity	NPD5405	Approved
0.6821	Remote Similarity	NPD5404	Approved
0.6818	Remote Similarity	NPD4360	Phase 2
0.6818	Remote Similarity	NPD2309	Approved
0.6818	Remote Similarity	NPD4363	Phase 3
0.6805	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD3764	Approved
0.6804	Remote Similarity	NPD6784	Approved
0.6804	Remote Similarity	NPD6785	Approved
0.6796	Remote Similarity	NPD6585	Discontinued
0.6786	Remote Similarity	NPD6832	Phase 2
0.678	Remote Similarity	NPD7236	Approved
0.678	Remote Similarity	NPD3300	Phase 2
0.6778	Remote Similarity	NPD1653	Approved
0.6763	Remote Similarity	NPD7033	Discontinued
0.6763	Remote Similarity	NPD4308	Phase 3

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