NPASS Compound

Structure

NPC476216 OpenBabel07101718272D 46 52 0 0 1 0 0 0 0 0999 V2000 -1.2492 3.3053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8849 3.3053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0784 -1.8160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9847 3.6925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0227 -0.1245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5505 0.6933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6674 0.0718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0075 -1.5281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0670 1.8887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2940 -0.7471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4313 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2940 -0.4981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2461 2.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4555 1.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8627 -0.7471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0212 -0.4505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3024 -0.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0670 2.8331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0784 -0.8716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1941 3.1760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1676 -0.2490 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4313 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8627 -0.4981 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.0784 -0.3736 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.2157 -0.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9797 -0.6796 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6470 -0.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2157 -0.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.4981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4313 -0.4981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6470 -0.1245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2157 -0.1245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0763 0.4248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3515 3.6024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0784 -0.1245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7437 -0.1245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5075 0.7736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2157 -0.1245 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.4424 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4313 -1.4424 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8644 0.9451 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2995 4.5453 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4391 3.0859 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8627 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 1.4519 0.7736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 35 1 0 0 0 0 6 35 1 0 0 0 0 7 36 1 0 0 0 0 8 36 1 0 0 0 0 9 11 1 0 0 0 0 9 18 2 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 14 1 0 0 0 0 13 20 2 0 0 0 0 14 37 1 0 0 0 0 15 19 2 0 0 0 0 15 23 1 0 0 0 0 16 25 2 0 0 0 0 17 21 1 0 0 0 0 17 26 1 0 0 0 0 20 34 1 0 0 0 0 21 16 1 1 0 0 0 21 33 1 0 0 0 0 22 31 2 0 0 0 0 22 32 1 0 0 0 0 23 24 1 0 0 0 0 23 27 1 0 0 0 0 24 35 1 0 0 0 0 25 29 1 0 0 0 0 26 36 1 0 0 0 0 26 38 1 1 0 0 0 27 30 2 0 0 0 0 27 31 1 0 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 39 2 0 0 0 0 30 40 1 0 0 0 0 31 44 1 0 0 0 0 32 45 1 0 0 0 0 33 37 1 0 0 0 0 33 41 2 0 0 0 0 34 42 2 0 0 0 0 34 43 1 0 0 0 0 35 44 1 0 0 0 0 36 46 1 0 0 0 0 37 38 1 1 0 0 0 37 46 1 0 0 0 0 38 25 1 6 0 0 0 38 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	628.3
Volume:	649.866
LogP:	8.038
LogD:	3.778
LogS:	-2.044
# Rotatable Bonds:	5
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.342
Synthetic Accessibility Score:	7.048
Fsp3:	0.553
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:	-4.794
MDCK Permeability:	1.8557109797257e-05
Pgp-inhibitor:	0.939
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.36
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.166

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.202
Plasma Protein Binding (PPB):	95.60543060302734%
Volume Distribution (VD):	1.286
Pgp-substrate:	5.0034332275390625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.622
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.841
CYP2C9-inhibitor:	0.449
CYP2C9-substrate:	0.329
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.358
CYP3A4-substrate:	0.867

ADMET: Excretion

Clearance (CL):	1.065
Half-life (T1/2):	0.015

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.962
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.114
Carcinogencity:	0.947
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC476216

Natural Product ID:	NPC476216
*Common Name:**	Gambogefic Acid
IUPAC Name:	n.a.
Synonyms:	Gambogefic Acid
Standard InCHIKey:	FJRORJDZZLUAPP-BUJCIKCXSA-N
Standard InCHI:	InChI=1S/C38H44O8/c1-18(2)9-11-22-31-27(23-15-19(3)10-12-24(23)35(5,6)44-31)30(40)28-29(39)25-16-21-17-26-36(7,8)46-37(33(21)41,14-13-20(4)34(42)43)38(25,26)45-32(22)28/h9,13,15-16,21,23-24,26,40H,10-12,14,17H2,1-8H3,(H,42,43)/b20-13-/t21-,23?,24?,26+,37+,38-/m1/s1
SMILES:	CC1=CC2C(CC1)C(OC3=C(C4=C(C(=C23)O)C(=O)C5=CC6CC7C5(O4)C(C6=O)(OC7(C)C)CC=C(C)C(=O)O)CC=C(C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL554811
PubChem CID:	25208438
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	=	560.0	nM	PMID[543314]

☑ 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 NPC476216 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	1668
0.2-0.3	3334
0.3-0.4	7177
0.4-0.5	10894
0.5-0.6	6230
0.6-0.7	5981
0.7-0.8	6739
0.8-0.85	195
0.85-0.9	30
0.9-0.95	28
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9874	High Similarity	NPC41598
0.9814	High Similarity	NPC476139
0.981	High Similarity	NPC189689
0.975	High Similarity	NPC55422
0.975	High Similarity	NPC476146
0.975	High Similarity	NPC47634
0.975	High Similarity	NPC75141
0.975	High Similarity	NPC40089
0.975	High Similarity	NPC158329
0.9571	High Similarity	NPC476229
0.9571	High Similarity	NPC476152
0.9568	High Similarity	NPC476196
0.9557	High Similarity	NPC286422
0.95	High Similarity	NPC131578
0.9394	High Similarity	NPC162248
0.9333	High Similarity	NPC476311
0.9325	High Similarity	NPC223413
0.9317	High Similarity	NPC94796
0.9281	High Similarity	NPC476210
0.9281	High Similarity	NPC233978
0.9281	High Similarity	NPC476199
0.9273	High Similarity	NPC476159
0.9264	High Similarity	NPC476255
0.9226	High Similarity	NPC473607
0.9193	High Similarity	NPC43490
0.9193	High Similarity	NPC475107
0.9152	High Similarity	NPC63514
0.9146	High Similarity	NPC62444
0.9146	High Similarity	NPC476056
0.9112	High Similarity	NPC473729
0.9107	High Similarity	NPC227275
0.9091	High Similarity	NPC193222
0.9042	High Similarity	NPC169018
0.9036	High Similarity	NPC102810
0.8994	High Similarity	NPC98943
0.8994	High Similarity	NPC476162
0.8909	High Similarity	NPC476931
0.8876	High Similarity	NPC475080
0.8834	High Similarity	NPC476930
0.8824	High Similarity	NPC475398
0.8706	High Similarity	NPC118128
0.8675	High Similarity	NPC476929
0.8663	High Similarity	NPC469345
0.8655	High Similarity	NPC17105
0.8655	High Similarity	NPC474276
0.8655	High Similarity	NPC73899
0.8655	High Similarity	NPC147363
0.8647	High Similarity	NPC193698
0.8639	High Similarity	NPC292233
0.8631	High Similarity	NPC473908
0.8623	High Similarity	NPC475106
0.8605	High Similarity	NPC86809
0.8605	High Similarity	NPC98667
0.8605	High Similarity	NPC294149
0.8605	High Similarity	NPC232412
0.8596	High Similarity	NPC477529
0.8588	High Similarity	NPC207574
0.8588	High Similarity	NPC297195
0.8588	High Similarity	NPC291795
0.858	High Similarity	NPC475109
0.8563	High Similarity	NPC61382
0.8563	High Similarity	NPC103816
0.8547	High Similarity	NPC469393
0.8538	High Similarity	NPC251144
0.8538	High Similarity	NPC241387
0.8506	High Similarity	NPC477683
0.8506	High Similarity	NPC477682
0.8494	Intermediate Similarity	NPC201127
0.8488	Intermediate Similarity	NPC472620
0.8481	Intermediate Similarity	NPC469818
0.848	Intermediate Similarity	NPC472619
0.848	Intermediate Similarity	NPC54903
0.848	Intermediate Similarity	NPC286074
0.8471	Intermediate Similarity	NPC17274
0.8471	Intermediate Similarity	NPC85047
0.8471	Intermediate Similarity	NPC120857
0.8466	Intermediate Similarity	NPC475656
0.8466	Intermediate Similarity	NPC475148
0.8447	Intermediate Similarity	NPC470676
0.8447	Intermediate Similarity	NPC473132
0.8447	Intermediate Similarity	NPC473135
0.8443	Intermediate Similarity	NPC125969
0.8443	Intermediate Similarity	NPC474373
0.8427	Intermediate Similarity	NPC174486
0.8421	Intermediate Similarity	NPC472622
0.8418	Intermediate Similarity	NPC106700
0.8409	Intermediate Similarity	NPC208069
0.8402	Intermediate Similarity	NPC473022
0.84	Intermediate Similarity	NPC5671
0.8393	Intermediate Similarity	NPC172687
0.8393	Intermediate Similarity	NPC243701
0.8383	Intermediate Similarity	NPC474637
0.8383	Intermediate Similarity	NPC161650
0.8373	Intermediate Similarity	NPC469934
0.8372	Intermediate Similarity	NPC20734
0.8363	Intermediate Similarity	NPC472621
0.8363	Intermediate Similarity	NPC469394
0.8354	Intermediate Similarity	NPC476509
0.8354	Intermediate Similarity	NPC150928
0.8352	Intermediate Similarity	NPC470200
0.8352	Intermediate Similarity	NPC470194
0.8352	Intermediate Similarity	NPC316274
0.8352	Intermediate Similarity	NPC470195
0.8352	Intermediate Similarity	NPC282474
0.8352	Intermediate Similarity	NPC470197
0.8352	Intermediate Similarity	NPC470193
0.8352	Intermediate Similarity	NPC470196
0.8352	Intermediate Similarity	NPC470198
0.8343	Intermediate Similarity	NPC324220
0.8343	Intermediate Similarity	NPC312630
0.8333	Intermediate Similarity	NPC264932
0.8333	Intermediate Similarity	NPC311574
0.8333	Intermediate Similarity	NPC154986
0.8324	Intermediate Similarity	NPC282636
0.8324	Intermediate Similarity	NPC313717
0.8324	Intermediate Similarity	NPC294863
0.8324	Intermediate Similarity	NPC315306
0.8313	Intermediate Similarity	NPC472799
0.8313	Intermediate Similarity	NPC477669
0.8304	Intermediate Similarity	NPC316262
0.8304	Intermediate Similarity	NPC314653
0.8287	Intermediate Similarity	NPC48474
0.8286	Intermediate Similarity	NPC245975
0.8276	Intermediate Similarity	NPC473113
0.8276	Intermediate Similarity	NPC91650
0.8274	Intermediate Similarity	NPC210048
0.8268	Intermediate Similarity	NPC197972
0.8266	Intermediate Similarity	NPC473096
0.8266	Intermediate Similarity	NPC473095
0.8263	Intermediate Similarity	NPC471456
0.8263	Intermediate Similarity	NPC275575
0.8258	Intermediate Similarity	NPC182693
0.8256	Intermediate Similarity	NPC323137
0.8253	Intermediate Similarity	NPC470353
0.8249	Intermediate Similarity	NPC244903
0.8249	Intermediate Similarity	NPC473785
0.8249	Intermediate Similarity	NPC121888
0.8246	Intermediate Similarity	NPC469395
0.8242	Intermediate Similarity	NPC327059
0.8242	Intermediate Similarity	NPC470199
0.8242	Intermediate Similarity	NPC321387
0.8242	Intermediate Similarity	NPC314459
0.8239	Intermediate Similarity	NPC101991
0.8235	Intermediate Similarity	NPC117985
0.8235	Intermediate Similarity	NPC92589
0.8232	Intermediate Similarity	NPC295436
0.8232	Intermediate Similarity	NPC314672
0.8221	Intermediate Similarity	NPC82534
0.8214	Intermediate Similarity	NPC146636
0.8214	Intermediate Similarity	NPC164427
0.8214	Intermediate Similarity	NPC54830
0.8214	Intermediate Similarity	NPC4547
0.8214	Intermediate Similarity	NPC470352
0.8214	Intermediate Similarity	NPC470354
0.8214	Intermediate Similarity	NPC472050
0.8214	Intermediate Similarity	NPC477674
0.8214	Intermediate Similarity	NPC56049
0.8212	Intermediate Similarity	NPC476170
0.8208	Intermediate Similarity	NPC253730
0.8208	Intermediate Similarity	NPC471975
0.8208	Intermediate Similarity	NPC470374
0.8208	Intermediate Similarity	NPC126204
0.8208	Intermediate Similarity	NPC76647
0.8208	Intermediate Similarity	NPC470377
0.8208	Intermediate Similarity	NPC286230
0.8208	Intermediate Similarity	NPC478059
0.8208	Intermediate Similarity	NPC473094
0.8208	Intermediate Similarity	NPC478060
0.8204	Intermediate Similarity	NPC209760
0.8204	Intermediate Similarity	NPC192189
0.8204	Intermediate Similarity	NPC100134
0.8204	Intermediate Similarity	NPC471695
0.8198	Intermediate Similarity	NPC259007
0.8198	Intermediate Similarity	NPC475979
0.8198	Intermediate Similarity	NPC473010
0.8198	Intermediate Similarity	NPC204088
0.8198	Intermediate Similarity	NPC329215
0.8197	Intermediate Similarity	NPC314020
0.8193	Intermediate Similarity	NPC209142
0.8193	Intermediate Similarity	NPC477673
0.8193	Intermediate Similarity	NPC477672
0.8193	Intermediate Similarity	NPC305965
0.8193	Intermediate Similarity	NPC312549
0.8187	Intermediate Similarity	NPC241975
0.8187	Intermediate Similarity	NPC19476
0.8182	Intermediate Similarity	NPC198927
0.8182	Intermediate Similarity	NPC473978
0.8182	Intermediate Similarity	NPC469932
0.8182	Intermediate Similarity	NPC6923
0.8176	Intermediate Similarity	NPC195136
0.8176	Intermediate Similarity	NPC472055
0.8171	Intermediate Similarity	NPC140120
0.8171	Intermediate Similarity	NPC121333
0.8167	Intermediate Similarity	NPC112380
0.8166	Intermediate Similarity	NPC318527
0.8166	Intermediate Similarity	NPC263483
0.8166	Intermediate Similarity	NPC323627
0.8166	Intermediate Similarity	NPC324358
0.8166	Intermediate Similarity	NPC322459
0.8161	Intermediate Similarity	NPC152477

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 NPC476216 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	987
0.2-0.3	1985
0.3-0.4	2714
0.4-0.5	1895
0.5-0.6	836
0.6-0.7	264
0.7-0.8	120
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
0.8383	Intermediate Similarity	NPD7075	Discontinued
0.8204	Intermediate Similarity	NPD7819	Suspended
0.8204	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7411	Suspended
0.8057	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD2533	Approved
0.8049	Intermediate Similarity	NPD2532	Approved
0.8049	Intermediate Similarity	NPD2534	Approved
0.7963	Intermediate Similarity	NPD2800	Approved
0.7953	Intermediate Similarity	NPD3749	Approved
0.7943	Intermediate Similarity	NPD7473	Discontinued
0.7939	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD6801	Discontinued
0.7895	Intermediate Similarity	NPD3882	Suspended
0.7861	Intermediate Similarity	NPD5494	Approved
0.7831	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6959	Discontinued
0.7811	Intermediate Similarity	NPD6599	Discontinued
0.7802	Intermediate Similarity	NPD8434	Phase 2
0.7784	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6166	Phase 2
0.7784	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7808	Phase 3
0.7771	Intermediate Similarity	NPD6799	Approved
0.7771	Intermediate Similarity	NPD6232	Discontinued
0.7765	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD3817	Phase 2
0.7722	Intermediate Similarity	NPD7251	Discontinued
0.7706	Intermediate Similarity	NPD4380	Phase 2
0.7705	Intermediate Similarity	NPD8150	Discontinued
0.7701	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3750	Approved
0.7688	Intermediate Similarity	NPD7768	Phase 2
0.7688	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD1465	Phase 2
0.7674	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6797	Phase 2
0.7647	Intermediate Similarity	NPD3226	Approved
0.7611	Intermediate Similarity	NPD7074	Phase 3
0.7593	Intermediate Similarity	NPD6651	Approved
0.7582	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD5710	Approved
0.7571	Intermediate Similarity	NPD5711	Approved
0.7556	Intermediate Similarity	NPD7054	Approved
0.7556	Intermediate Similarity	NPD5844	Phase 1
0.7554	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD8313	Approved
0.7541	Intermediate Similarity	NPD8312	Approved
0.7529	Intermediate Similarity	NPD5403	Approved
0.7529	Intermediate Similarity	NPD5402	Approved
0.7527	Intermediate Similarity	NPD6559	Discontinued
0.7514	Intermediate Similarity	NPD7472	Approved
0.7514	Intermediate Similarity	NPD1934	Approved
0.75	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD919	Approved
0.7471	Intermediate Similarity	NPD2801	Approved
0.7471	Intermediate Similarity	NPD1512	Approved
0.747	Intermediate Similarity	NPD1549	Phase 2
0.7455	Intermediate Similarity	NPD6099	Approved
0.7455	Intermediate Similarity	NPD6100	Approved
0.7433	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD1243	Approved
0.7425	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD1247	Approved
0.7412	Intermediate Similarity	NPD5401	Approved
0.741	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2346	Discontinued
0.741	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2799	Discontinued
0.7394	Intermediate Similarity	NPD3748	Approved
0.7389	Intermediate Similarity	NPD2403	Approved
0.7353	Intermediate Similarity	NPD1511	Approved
0.7333	Intermediate Similarity	NPD3926	Phase 2
0.7333	Intermediate Similarity	NPD7435	Discontinued
0.7323	Intermediate Similarity	NPD8151	Discontinued
0.7308	Intermediate Similarity	NPD7228	Approved
0.7308	Intermediate Similarity	NPD3751	Discontinued
0.7292	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1510	Phase 2
0.7273	Intermediate Similarity	NPD1607	Approved
0.7256	Intermediate Similarity	NPD1240	Approved
0.7246	Intermediate Similarity	NPD2796	Approved
0.7245	Intermediate Similarity	NPD7698	Approved
0.7245	Intermediate Similarity	NPD7697	Approved
0.7245	Intermediate Similarity	NPD7696	Phase 3
0.7238	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD920	Approved
0.7208	Intermediate Similarity	NPD8320	Phase 1
0.7208	Intermediate Similarity	NPD8319	Approved
0.7202	Intermediate Similarity	NPD1471	Phase 3
0.72	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7874	Approved
0.7189	Intermediate Similarity	NPD5953	Discontinued
0.7186	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4287	Approved
0.7151	Intermediate Similarity	NPD7390	Discontinued
0.7143	Intermediate Similarity	NPD2935	Discontinued
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7134	Intermediate Similarity	NPD2313	Discontinued
0.7126	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7871	Phase 2
0.7121	Intermediate Similarity	NPD7870	Phase 2
0.7119	Intermediate Similarity	NPD37	Approved
0.7111	Intermediate Similarity	NPD6234	Discontinued
0.711	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5124	Phase 1
0.7108	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2344	Approved
0.7101	Intermediate Similarity	NPD8366	Approved
0.71	Intermediate Similarity	NPD7701	Phase 2
0.7095	Intermediate Similarity	NPD4967	Phase 2
0.7095	Intermediate Similarity	NPD4966	Approved
0.7095	Intermediate Similarity	NPD4965	Approved
0.7093	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6776	Approved
0.7092	Intermediate Similarity	NPD6777	Approved
0.7092	Intermediate Similarity	NPD6779	Approved
0.7092	Intermediate Similarity	NPD6782	Approved
0.7092	Intermediate Similarity	NPD6781	Approved
0.7092	Intermediate Similarity	NPD6780	Approved
0.7092	Intermediate Similarity	NPD6778	Approved
0.7088	Intermediate Similarity	NPD3787	Discontinued
0.7081	Intermediate Similarity	NPD7286	Phase 2
0.7079	Intermediate Similarity	NPD7783	Phase 2
0.7079	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7699	Phase 2
0.7077	Intermediate Similarity	NPD7700	Phase 2
0.7076	Intermediate Similarity	NPD4628	Phase 3
0.7041	Intermediate Similarity	NPD8285	Discontinued
0.7033	Intermediate Similarity	NPD7199	Phase 2
0.703	Intermediate Similarity	NPD3268	Approved
0.703	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7229	Phase 3
0.6995	Remote Similarity	NPD7801	Approved
0.6977	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7240	Approved
0.6967	Remote Similarity	NPD8491	Approved
0.6949	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5404	Approved
0.6941	Remote Similarity	NPD5405	Approved
0.6941	Remote Similarity	NPD5406	Approved
0.6941	Remote Similarity	NPD5408	Approved
0.6936	Remote Similarity	NPD2309	Approved
0.6934	Remote Similarity	NPD8469	Approved
0.6928	Remote Similarity	NPD3764	Approved
0.6923	Remote Similarity	NPD6535	Approved
0.6923	Remote Similarity	NPD6534	Approved
0.6919	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6355	Discontinued
0.6905	Remote Similarity	NPD447	Suspended
0.6889	Remote Similarity	NPD8455	Phase 2
0.6879	Remote Similarity	NPD7003	Approved
0.6878	Remote Similarity	NPD7685	Pre-registration
0.6878	Remote Similarity	NPD6765	Approved
0.6878	Remote Similarity	NPD6764	Approved
0.6875	Remote Similarity	NPD5049	Phase 3
0.6857	Remote Similarity	NPD7907	Approved
0.6857	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD4288	Approved
0.6848	Remote Similarity	NPD8127	Discontinued
0.6845	Remote Similarity	NPD4060	Phase 1
0.6845	Remote Similarity	NPD943	Approved
0.6845	Remote Similarity	NPD7799	Discontinued
0.6829	Remote Similarity	NPD1203	Approved
0.6826	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6585	Discontinued
0.681	Remote Similarity	NPD4749	Approved
0.6807	Remote Similarity	NPD6832	Phase 2
0.6805	Remote Similarity	NPD230	Phase 1
0.6802	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5761	Phase 2
0.6796	Remote Similarity	NPD5760	Phase 2
0.6792	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD4308	Phase 3
0.6782	Remote Similarity	NPD8166	Discontinued
0.6778	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD8407	Phase 2
0.6766	Remote Similarity	NPD4625	Phase 3
0.6766	Remote Similarity	NPD6823	Phase 2
0.6761	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD9717	Approved
0.6746	Remote Similarity	NPD8404	Phase 2
0.6743	Remote Similarity	NPD6190	Approved
0.6743	Remote Similarity	NPD2354	Approved
0.6736	Remote Similarity	NPD6784	Approved
0.6736	Remote Similarity	NPD6785	Approved
0.6727	Remote Similarity	NPD2797	Approved
0.6727	Remote Similarity	NPD3267	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