NPASS Compound

Structure

NPC99726 OpenBabel07101719522D 34 37 0 0 1 0 0 0 0 0999 V2000 -0.8767 -5.3851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1336 -2.8785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1733 2.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1996 2.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3361 -1.9261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2904 0.8895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2816 -3.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0052 -4.1318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4840 -2.5279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1848 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6125 0.3009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8027 -5.0842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4101 -2.2270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6865 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5297 1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5263 -5.7357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6125 -1.2746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6865 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8432 0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3729 1.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3239 -6.6881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4524 -5.4348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 8 9 1 0 0 0 0 8 10 2 0 0 0 0 9 19 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 22 2 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 25 1 0 0 0 0 20 2 1 1 0 0 0 20 27 1 0 0 0 0 21 26 1 0 0 0 0 21 29 1 1 0 0 0 22 27 1 0 0 0 0 22 28 1 0 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 31 1 6 0 0 0 25 32 2 0 0 0 0 25 33 1 0 0 0 0 27 5 1 1 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	517.825
LogP:	4.832
LogD:	3.058
LogS:	-4.072
# Rotatable Bonds:	4
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.333
Synthetic Accessibility Score:	5.342
Fsp3:	0.767
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.181
MDCK Permeability:	2.1867777832085267e-05
Pgp-inhibitor:	0.609
Pgp-substrate:	0.069
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.1

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.62
Plasma Protein Binding (PPB):	93.83235931396484%
Volume Distribution (VD):	0.68
Pgp-substrate:	5.886157512664795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.469
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.694
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.2
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.037
CYP3A4-inhibitor:	0.454
CYP3A4-substrate:	0.8

ADMET: Excretion

Clearance (CL):	2.898
Half-life (T1/2):	0.092

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.623
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.875
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.633
Carcinogencity:	0.748
Eye Corrosion:	0.004
Eye Irritation:	0.022
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC99726

Natural Product ID:	NPC99726
*Common Name:**	Garcihombronane G
IUPAC Name:	(2E,4Z,6R)-6-[(3R,5S,8S,9R,10S,14S,17S)-3,9-dihydroxy-4,4,10,14,17-pentamethyl-1,2,3,5,6,7,8,11,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-methylhepta-2,4-dienoic acid
Synonyms:	garcihombronane G
Standard InCHIKey:	QAAJVBKHQHFGTB-DQPQUSLRSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-19(25(32)33)9-8-10-20(2)27(5)17-18-28(6)22(27)13-16-30(34)23(28)12-11-21-26(3,4)24(31)14-15-29(21,30)7/h8-10,13,20-21,23-24,31,34H,11-12,14-18H2,1-7H3,(H,32,33)/b10-8-,19-9+/t20-,21+,23+,24-,27+,28-,29+,30-/m1/s1
SMILES:	C/C(=CC=C/[C@@H](C)[C@]1(C)CC[C@]2(C)C1=CC[C@]1([C@H]2CC[C@H]2C(C)(C)[C@@H](CC[C@]12C)O)O)/C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470244
PubChem CID:	11662818
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16124765]
NPO20779	Garcinia hombroniana	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[470996]

☑ 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 NPC99726 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	174
0.1-0.2	930
0.2-0.3	3658
0.3-0.4	8447
0.4-0.5	13533
0.5-0.6	7138
0.6-0.7	5853
0.7-0.8	2701
0.8-0.85	230
0.85-0.9	24
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC279410
0.9667	High Similarity	NPC119562
0.913	High Similarity	NPC214697
0.9022	High Similarity	NPC212948
0.9011	High Similarity	NPC146554
0.9011	High Similarity	NPC472240
0.9011	High Similarity	NPC262858
0.8947	High Similarity	NPC141401
0.8854	High Similarity	NPC218107
0.883	High Similarity	NPC476186
0.8804	High Similarity	NPC314727
0.8778	High Similarity	NPC109528
0.875	High Similarity	NPC108078
0.8723	High Similarity	NPC476304
0.8723	High Similarity	NPC38232
0.8687	High Similarity	NPC85742
0.8681	High Similarity	NPC261266
0.8667	High Similarity	NPC302360
0.866	High Similarity	NPC103051
0.8646	High Similarity	NPC190713
0.8646	High Similarity	NPC301534
0.8646	High Similarity	NPC250757
0.8617	High Similarity	NPC110923
0.8617	High Similarity	NPC74296
0.8602	High Similarity	NPC16265
0.8557	High Similarity	NPC320306
0.8556	High Similarity	NPC57370
0.8495	Intermediate Similarity	NPC7280
0.8495	Intermediate Similarity	NPC229612
0.8485	Intermediate Similarity	NPC282524
0.8478	Intermediate Similarity	NPC6391
0.8469	Intermediate Similarity	NPC114274
0.8462	Intermediate Similarity	NPC255401
0.8462	Intermediate Similarity	NPC284162
0.8454	Intermediate Similarity	NPC276103
0.8454	Intermediate Similarity	NPC195366
0.8454	Intermediate Similarity	NPC114743
0.8454	Intermediate Similarity	NPC54248
0.8444	Intermediate Similarity	NPC224455
0.8444	Intermediate Similarity	NPC2524
0.8438	Intermediate Similarity	NPC474922
0.8438	Intermediate Similarity	NPC299100
0.8438	Intermediate Similarity	NPC469406
0.84	Intermediate Similarity	NPC293753
0.8384	Intermediate Similarity	NPC470074
0.8384	Intermediate Similarity	NPC327431
0.8384	Intermediate Similarity	NPC266955
0.8352	Intermediate Similarity	NPC79945
0.8351	Intermediate Similarity	NPC271195
0.8351	Intermediate Similarity	NPC180950
0.835	Intermediate Similarity	NPC304276
0.835	Intermediate Similarity	NPC137462
0.8333	Intermediate Similarity	NPC152778
0.8333	Intermediate Similarity	NPC162615
0.8333	Intermediate Similarity	NPC159148
0.8333	Intermediate Similarity	NPC205034
0.8317	Intermediate Similarity	NPC247957
0.8317	Intermediate Similarity	NPC249187
0.8317	Intermediate Similarity	NPC475050
0.8317	Intermediate Similarity	NPC171014
0.8317	Intermediate Similarity	NPC297617
0.8316	Intermediate Similarity	NPC295668
0.8316	Intermediate Similarity	NPC310479
0.8316	Intermediate Similarity	NPC182136
0.8316	Intermediate Similarity	NPC221111
0.8316	Intermediate Similarity	NPC280149
0.83	Intermediate Similarity	NPC115899
0.8286	Intermediate Similarity	NPC262083
0.8286	Intermediate Similarity	NPC471484
0.8283	Intermediate Similarity	NPC57079
0.8283	Intermediate Similarity	NPC92275
0.8283	Intermediate Similarity	NPC108368
0.8283	Intermediate Similarity	NPC166745
0.8283	Intermediate Similarity	NPC235464
0.828	Intermediate Similarity	NPC475069
0.828	Intermediate Similarity	NPC175145
0.828	Intermediate Similarity	NPC474970
0.8265	Intermediate Similarity	NPC473153
0.8265	Intermediate Similarity	NPC16967
0.8261	Intermediate Similarity	NPC231310
0.8261	Intermediate Similarity	NPC238485
0.8261	Intermediate Similarity	NPC205845
0.8261	Intermediate Similarity	NPC33913
0.8252	Intermediate Similarity	NPC472925
0.8247	Intermediate Similarity	NPC474690
0.8247	Intermediate Similarity	NPC191521
0.8247	Intermediate Similarity	NPC8993
0.8247	Intermediate Similarity	NPC57117
0.8242	Intermediate Similarity	NPC49964
0.8242	Intermediate Similarity	NPC50964
0.8229	Intermediate Similarity	NPC234335
0.8229	Intermediate Similarity	NPC41554
0.8229	Intermediate Similarity	NPC97404
0.8229	Intermediate Similarity	NPC475806
0.8229	Intermediate Similarity	NPC177641
0.8222	Intermediate Similarity	NPC281880
0.8218	Intermediate Similarity	NPC234892
0.8218	Intermediate Similarity	NPC136289
0.8211	Intermediate Similarity	NPC257485
0.8208	Intermediate Similarity	NPC44537
0.82	Intermediate Similarity	NPC251680
0.82	Intermediate Similarity	NPC154072
0.8191	Intermediate Similarity	NPC475772
0.819	Intermediate Similarity	NPC12795
0.819	Intermediate Similarity	NPC103491
0.8182	Intermediate Similarity	NPC474938
0.8182	Intermediate Similarity	NPC253826
0.8182	Intermediate Similarity	NPC474785
0.8173	Intermediate Similarity	NPC472217
0.8173	Intermediate Similarity	NPC472219
0.8173	Intermediate Similarity	NPC472218
0.8173	Intermediate Similarity	NPC275060
0.8172	Intermediate Similarity	NPC470360
0.8163	Intermediate Similarity	NPC276110
0.8155	Intermediate Similarity	NPC295843
0.8155	Intermediate Similarity	NPC323834
0.8155	Intermediate Similarity	NPC257353
0.8152	Intermediate Similarity	NPC476927
0.8144	Intermediate Similarity	NPC310013
0.8137	Intermediate Similarity	NPC478057
0.8137	Intermediate Similarity	NPC23584
0.8137	Intermediate Similarity	NPC72151
0.8137	Intermediate Similarity	NPC95899
0.8137	Intermediate Similarity	NPC45897
0.8132	Intermediate Similarity	NPC23852
0.8132	Intermediate Similarity	NPC264245
0.8132	Intermediate Similarity	NPC476646
0.8132	Intermediate Similarity	NPC209620
0.8125	Intermediate Similarity	NPC329596
0.8125	Intermediate Similarity	NPC48010
0.8125	Intermediate Similarity	NPC204188
0.8125	Intermediate Similarity	NPC3345
0.8125	Intermediate Similarity	NPC291484
0.8125	Intermediate Similarity	NPC80561
0.8125	Intermediate Similarity	NPC11216
0.8125	Intermediate Similarity	NPC78973
0.8125	Intermediate Similarity	NPC469400
0.8119	Intermediate Similarity	NPC268829
0.8119	Intermediate Similarity	NPC81530
0.8119	Intermediate Similarity	NPC472924
0.8119	Intermediate Similarity	NPC247701
0.8119	Intermediate Similarity	NPC25177
0.8119	Intermediate Similarity	NPC222875
0.8119	Intermediate Similarity	NPC295110
0.8113	Intermediate Similarity	NPC474315
0.8113	Intermediate Similarity	NPC183603
0.8113	Intermediate Similarity	NPC470076
0.8105	Intermediate Similarity	NPC133588
0.8105	Intermediate Similarity	NPC280556
0.8105	Intermediate Similarity	NPC104560
0.8105	Intermediate Similarity	NPC474668
0.81	Intermediate Similarity	NPC471717
0.81	Intermediate Similarity	NPC478056
0.81	Intermediate Similarity	NPC186810
0.81	Intermediate Similarity	NPC48647
0.81	Intermediate Similarity	NPC477854
0.81	Intermediate Similarity	NPC278673
0.8095	Intermediate Similarity	NPC75389
0.8085	Intermediate Similarity	NPC82979
0.8085	Intermediate Similarity	NPC299068
0.8085	Intermediate Similarity	NPC293287
0.8085	Intermediate Similarity	NPC152808
0.8081	Intermediate Similarity	NPC249954
0.8081	Intermediate Similarity	NPC7124
0.8081	Intermediate Similarity	NPC477853
0.8081	Intermediate Similarity	NPC472941
0.8081	Intermediate Similarity	NPC456
0.8077	Intermediate Similarity	NPC473284
0.8077	Intermediate Similarity	NPC79298
0.8077	Intermediate Similarity	NPC43063
0.8065	Intermediate Similarity	NPC472265
0.8065	Intermediate Similarity	NPC474493
0.8061	Intermediate Similarity	NPC105490
0.8061	Intermediate Similarity	NPC470957
0.8061	Intermediate Similarity	NPC201725
0.8061	Intermediate Similarity	NPC292793
0.8061	Intermediate Similarity	NPC470958
0.8061	Intermediate Similarity	NPC196485
0.8061	Intermediate Similarity	NPC245972
0.8061	Intermediate Similarity	NPC469491
0.8058	Intermediate Similarity	NPC472868
0.8058	Intermediate Similarity	NPC72255
0.8058	Intermediate Similarity	NPC473543
0.8043	Intermediate Similarity	NPC256112
0.8043	Intermediate Similarity	NPC218616
0.8043	Intermediate Similarity	NPC296701
0.8043	Intermediate Similarity	NPC202389
0.8043	Intermediate Similarity	NPC87489
0.8043	Intermediate Similarity	NPC101462
0.8041	Intermediate Similarity	NPC473675
0.8041	Intermediate Similarity	NPC204341
0.8041	Intermediate Similarity	NPC477574
0.8041	Intermediate Similarity	NPC473998
0.8041	Intermediate Similarity	NPC233116
0.8039	Intermediate Similarity	NPC155332
0.8039	Intermediate Similarity	NPC32577
0.8039	Intermediate Similarity	NPC475038
0.8039	Intermediate Similarity	NPC11956
0.8039	Intermediate Similarity	NPC114540
0.8039	Intermediate Similarity	NPC320447

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 NPC99726 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1070
0.2-0.3	3579
0.3-0.4	2829
0.4-0.5	983
0.5-0.6	226
0.6-0.7	172
0.7-0.8	144
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
0.82	Intermediate Similarity	NPD7639	Approved
0.82	Intermediate Similarity	NPD7640	Approved
0.81	Intermediate Similarity	NPD7638	Approved
0.7857	Intermediate Similarity	NPD7637	Suspended
0.7857	Intermediate Similarity	NPD6079	Approved
0.7748	Intermediate Similarity	NPD7115	Discovery
0.7692	Intermediate Similarity	NPD5211	Phase 2
0.7677	Intermediate Similarity	NPD7515	Phase 2
0.7664	Intermediate Similarity	NPD6881	Approved
0.7664	Intermediate Similarity	NPD6899	Approved
0.7653	Intermediate Similarity	NPD5328	Approved
0.7634	Intermediate Similarity	NPD7525	Registered
0.7634	Intermediate Similarity	NPD6931	Approved
0.7634	Intermediate Similarity	NPD6930	Phase 2
0.7634	Intermediate Similarity	NPD7514	Phase 3
0.7629	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD6695	Phase 3
0.7573	Intermediate Similarity	NPD4225	Approved
0.757	Intermediate Similarity	NPD5697	Approved
0.7549	Intermediate Similarity	NPD5222	Approved
0.7549	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD5221	Approved
0.7547	Intermediate Similarity	NPD5141	Approved
0.7527	Intermediate Similarity	NPD6929	Approved
0.7526	Intermediate Similarity	NPD3618	Phase 1
0.7524	Intermediate Similarity	NPD7632	Discontinued
0.7523	Intermediate Similarity	NPD7102	Approved
0.7523	Intermediate Similarity	NPD7290	Approved
0.7523	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD5286	Approved
0.75	Intermediate Similarity	NPD6011	Approved
0.75	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4786	Approved
0.75	Intermediate Similarity	NPD4696	Approved
0.75	Intermediate Similarity	NPD5285	Approved
0.7478	Intermediate Similarity	NPD7503	Approved
0.7477	Intermediate Similarity	NPD4632	Approved
0.7477	Intermediate Similarity	NPD5739	Approved
0.7477	Intermediate Similarity	NPD6675	Approved
0.7477	Intermediate Similarity	NPD7128	Approved
0.7477	Intermediate Similarity	NPD6402	Approved
0.7476	Intermediate Similarity	NPD5173	Approved
0.7473	Intermediate Similarity	NPD6942	Approved
0.7473	Intermediate Similarity	NPD7339	Approved
0.7455	Intermediate Similarity	NPD6847	Approved
0.7455	Intermediate Similarity	NPD8130	Phase 1
0.7455	Intermediate Similarity	NPD6617	Approved
0.7455	Intermediate Similarity	NPD6650	Approved
0.7455	Intermediate Similarity	NPD6869	Approved
0.7455	Intermediate Similarity	NPD6649	Approved
0.7447	Intermediate Similarity	NPD7332	Phase 2
0.7431	Intermediate Similarity	NPD6013	Approved
0.7431	Intermediate Similarity	NPD6012	Approved
0.7431	Intermediate Similarity	NPD6014	Approved
0.7429	Intermediate Similarity	NPD5223	Approved
0.7426	Intermediate Similarity	NPD4202	Approved
0.7426	Intermediate Similarity	NPD6399	Phase 3
0.7419	Intermediate Similarity	NPD7145	Approved
0.7387	Intermediate Similarity	NPD6882	Approved
0.7387	Intermediate Similarity	NPD8297	Approved
0.7368	Intermediate Similarity	NPD6902	Approved
0.7363	Intermediate Similarity	NPD6924	Approved
0.7363	Intermediate Similarity	NPD6926	Approved
0.7358	Intermediate Similarity	NPD5224	Approved
0.7358	Intermediate Similarity	NPD5226	Approved
0.7358	Intermediate Similarity	NPD5225	Approved
0.7358	Intermediate Similarity	NPD4633	Approved
0.7353	Intermediate Similarity	NPD7748	Approved
0.734	Intermediate Similarity	NPD4195	Approved
0.7339	Intermediate Similarity	NPD7320	Approved
0.7327	Intermediate Similarity	NPD5281	Approved
0.7327	Intermediate Similarity	NPD5284	Approved
0.7312	Intermediate Similarity	NPD6932	Approved
0.7312	Intermediate Similarity	NPD6925	Approved
0.7312	Intermediate Similarity	NPD5776	Phase 2
0.7308	Intermediate Similarity	NPD4755	Approved
0.7308	Intermediate Similarity	NPD6083	Phase 2
0.7308	Intermediate Similarity	NPD6084	Phase 2
0.7292	Intermediate Similarity	NPD3667	Approved
0.729	Intermediate Similarity	NPD5174	Approved
0.729	Intermediate Similarity	NPD5175	Approved
0.7283	Intermediate Similarity	NPD8264	Approved
0.7281	Intermediate Similarity	NPD6009	Approved
0.7273	Intermediate Similarity	NPD7750	Discontinued
0.7273	Intermediate Similarity	NPD7524	Approved
0.7273	Intermediate Similarity	NPD6373	Approved
0.7273	Intermediate Similarity	NPD6372	Approved
0.7255	Intermediate Similarity	NPD5779	Approved
0.7255	Intermediate Similarity	NPD5778	Approved
0.7248	Intermediate Similarity	NPD5701	Approved
0.7245	Intermediate Similarity	NPD6893	Approved
0.7245	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4697	Phase 3
0.7207	Intermediate Similarity	NPD4634	Approved
0.7204	Intermediate Similarity	NPD6933	Approved
0.7204	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5279	Phase 3
0.717	Intermediate Similarity	NPD4700	Approved
0.717	Intermediate Similarity	NPD6648	Approved
0.7156	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD3665	Phase 1
0.7143	Intermediate Similarity	NPD7152	Approved
0.7143	Intermediate Similarity	NPD3133	Approved
0.7143	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7150	Approved
0.7143	Intermediate Similarity	NPD3666	Approved
0.7143	Intermediate Similarity	NPD7151	Approved
0.7129	Intermediate Similarity	NPD6051	Approved
0.7129	Intermediate Similarity	NPD4753	Phase 2
0.7115	Intermediate Similarity	NPD5210	Approved
0.7115	Intermediate Similarity	NPD4629	Approved
0.7103	Intermediate Similarity	NPD5344	Discontinued
0.7094	Intermediate Similarity	NPD6319	Approved
0.7071	Intermediate Similarity	NPD1696	Phase 3
0.7069	Intermediate Similarity	NPD7327	Approved
0.7069	Intermediate Similarity	NPD7328	Approved
0.7069	Intermediate Similarity	NPD6335	Approved
0.7059	Intermediate Similarity	NPD7604	Phase 2
0.7043	Intermediate Similarity	NPD6868	Approved
0.7034	Intermediate Similarity	NPD5983	Phase 2
0.7034	Intermediate Similarity	NPD8033	Approved
0.7033	Intermediate Similarity	NPD7143	Approved
0.7033	Intermediate Similarity	NPD7144	Approved
0.703	Intermediate Similarity	NPD5737	Approved
0.703	Intermediate Similarity	NPD6672	Approved
0.7027	Intermediate Similarity	NPD4729	Approved
0.7027	Intermediate Similarity	NPD4730	Approved
0.701	Intermediate Similarity	NPD6898	Phase 1
0.7009	Intermediate Similarity	NPD6404	Discontinued
0.7009	Intermediate Similarity	NPD7101	Approved
0.7009	Intermediate Similarity	NPD7100	Approved
0.7009	Intermediate Similarity	NPD7516	Approved
0.7	Intermediate Similarity	NPD7492	Approved
0.7	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4519	Discontinued
0.7	Intermediate Similarity	NPD7146	Approved
0.7	Intermediate Similarity	NPD6684	Approved
0.7	Intermediate Similarity	NPD4623	Approved
0.7	Intermediate Similarity	NPD7521	Approved
0.7	Intermediate Similarity	NPD5330	Approved
0.7	Intermediate Similarity	NPD6409	Approved
0.7	Intermediate Similarity	NPD7334	Approved
0.699	Remote Similarity	NPD6411	Approved
0.699	Remote Similarity	NPD7087	Discontinued
0.6989	Remote Similarity	NPD4785	Approved
0.6989	Remote Similarity	NPD4784	Approved
0.6983	Remote Similarity	NPD6317	Approved
0.6979	Remote Similarity	NPD7645	Phase 2
0.6979	Remote Similarity	NPD6683	Phase 2
0.6972	Remote Similarity	NPD4754	Approved
0.6964	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5695	Phase 3
0.6949	Remote Similarity	NPD8294	Approved
0.6949	Remote Similarity	NPD6054	Approved
0.6949	Remote Similarity	NPD8377	Approved
0.6942	Remote Similarity	NPD6336	Discontinued
0.6942	Remote Similarity	NPD6616	Approved
0.6939	Remote Similarity	NPD4223	Phase 3
0.6939	Remote Similarity	NPD4221	Approved
0.6931	Remote Similarity	NPD3573	Approved
0.6923	Remote Similarity	NPD6923	Approved
0.6923	Remote Similarity	NPD6314	Approved
0.6923	Remote Similarity	NPD6313	Approved
0.6923	Remote Similarity	NPD6922	Approved
0.6916	Remote Similarity	NPD5290	Discontinued
0.6916	Remote Similarity	NPD5696	Approved
0.6907	Remote Similarity	NPD7509	Discontinued
0.6903	Remote Similarity	NPD5249	Phase 3
0.6903	Remote Similarity	NPD5250	Approved
0.6903	Remote Similarity	NPD5169	Approved
0.6903	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5251	Approved
0.6903	Remote Similarity	NPD5248	Approved
0.6903	Remote Similarity	NPD5247	Approved
0.6903	Remote Similarity	NPD5135	Approved
0.69	Remote Similarity	NPD5329	Approved
0.6897	Remote Similarity	NPD6274	Approved
0.6891	Remote Similarity	NPD8379	Approved
0.6891	Remote Similarity	NPD8335	Approved
0.6891	Remote Similarity	NPD8296	Approved
0.6891	Remote Similarity	NPD8380	Approved
0.6891	Remote Similarity	NPD8378	Approved
0.6885	Remote Similarity	NPD7078	Approved
0.6875	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5168	Approved
0.6875	Remote Similarity	NPD6115	Approved
0.6875	Remote Similarity	NPD6697	Approved
0.6875	Remote Similarity	NPD5128	Approved
0.6875	Remote Similarity	NPD6686	Approved
0.6875	Remote Similarity	NPD6118	Approved
0.6875	Remote Similarity	NPD6114	Approved
0.6863	Remote Similarity	NPD6903	Approved
0.6863	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7900	Approved
0.6847	Remote Similarity	NPD4768	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