NPASS Compound

Structure

NPC112167 OpenBabel07101719252D 34 38 0 0 1 0 0 0 0 0999 V2000 7.0569 -2.5806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6968 -0.8864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1006 -2.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1225 -3.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0141 -2.1381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1131 -2.5719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1285 -2.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 -2.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -2.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -3.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3173 0.1525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7512 -0.7485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -3.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7405 -1.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -0.3765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3878 -1.8375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4096 -2.0454 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4533 -2.4612 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7568 -0.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -2.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1906 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3201 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7624 -1.5102 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1878 -1.5747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8862 1.1282 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0932 -0.7670 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 18 2 0 0 0 0 2 18 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 26 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 13 2 0 0 0 0 12 24 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 19 1 0 0 0 0 15 25 1 0 0 0 0 16 21 1 0 0 0 0 17 27 1 0 0 0 0 17 30 1 0 0 0 0 18 19 1 0 0 0 0 19 3 1 1 0 0 0 20 4 1 1 0 0 0 20 22 1 0 0 0 0 20 25 1 0 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 22 30 1 1 0 0 0 23 28 1 0 0 0 0 24 32 2 0 0 0 0 25 33 1 6 0 0 0 26 29 1 6 0 0 0 26 31 1 0 0 0 0 27 31 1 1 0 0 0 27 34 1 0 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 31 16 1 1 0 0 0 31 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.34
Volume:	517.775
LogP:	6.812
LogD:	4.869
LogS:	-6.706
# Rotatable Bonds:	5
TPSA:	49.83
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.364
Synthetic Accessibility Score:	6.009
Fsp3:	0.774
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.82
MDCK Permeability:	2.29689285333734e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.125
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.245
Plasma Protein Binding (PPB):	94.67764282226562%
Volume Distribution (VD):	2.995
Pgp-substrate:	3.8117594718933105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.325
CYP2C19-inhibitor:	0.12
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.252
CYP2C9-substrate:	0.117
CYP2D6-inhibitor:	0.465
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.954
CYP3A4-substrate:	0.795

ADMET: Excretion

Clearance (CL):	9.205
Half-life (T1/2):	0.033

ADMET: Toxicity

hERG Blockers:	0.386
Human Hepatotoxicity (H-HT):	0.41
Drug-inuced Liver Injury (DILI):	0.245
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.65
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.16
Carcinogencity:	0.731
Eye Corrosion:	0.01
Eye Irritation:	0.04
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC112167

Natural Product ID:	NPC112167
*Common Name:**	FNMHRGADXLFVOB-FSJTZFQCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FNMHRGADXLFVOB-FSJTZFQCSA-N
Standard InCHI:	InChI=1S/C31H46O3/c1-18(2)19(3)15-25(33)20(4)22-11-14-29(7)26-10-9-23-21(24(32)12-13-28(23,5)6)16-31(26)27(34-31)17-30(22,29)8/h12-13,19-20,22,25-27,33H,1,9-11,14-17H2,2-8H3/t19-,20-,22+,25+,26-,27+,29-,30+,31-/m0/s1
SMILES:	O[C@@H]([C@H]([C@H]1CC[C@@]2([C@]1(C)C[C@H]1O[C@]31[C@H]2CCC1=C(C3)C(=O)C=CC1(C)C)C)C)C[C@@H](C(=C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419873
PubChem CID:	73350762
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[24033131]
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	twigs	n.a.	n.a.	PMID[25286284]
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26699618]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	=	78400.0	nM	PMID[543803]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	37700.0	nM	PMID[543803]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	73800.0	nM	PMID[543803]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	26100.0	nM	PMID[543803]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	22500.0	nM	PMID[543803]

☑ 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 NPC112167 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	200
0.1-0.2	1246
0.2-0.3	5234
0.3-0.4	12140
0.4-0.5	9867
0.5-0.6	7155
0.6-0.7	5141
0.7-0.8	1652
0.8-0.85	58
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8617	High Similarity	NPC86319
0.8617	High Similarity	NPC275740
0.8557	High Similarity	NPC259286
0.8511	High Similarity	NPC471722
0.8511	High Similarity	NPC131470
0.8511	High Similarity	NPC143767
0.8511	High Similarity	NPC328539
0.85	High Similarity	NPC476240
0.85	High Similarity	NPC237190
0.85	High Similarity	NPC224720
0.85	High Similarity	NPC476223
0.8469	Intermediate Similarity	NPC249954
0.8438	Intermediate Similarity	NPC272746
0.8421	Intermediate Similarity	NPC119416
0.8411	Intermediate Similarity	NPC238667
0.8404	Intermediate Similarity	NPC475740
0.8404	Intermediate Similarity	NPC58063
0.84	Intermediate Similarity	NPC476274
0.8387	Intermediate Similarity	NPC202868
0.837	Intermediate Similarity	NPC476082
0.837	Intermediate Similarity	NPC278648
0.8367	Intermediate Similarity	NPC470016
0.8367	Intermediate Similarity	NPC317586
0.8351	Intermediate Similarity	NPC134826
0.8351	Intermediate Similarity	NPC69454
0.8333	Intermediate Similarity	NPC191684
0.8333	Intermediate Similarity	NPC183283
0.83	Intermediate Similarity	NPC114274
0.8298	Intermediate Similarity	NPC475022
0.8298	Intermediate Similarity	NPC145879
0.8298	Intermediate Similarity	NPC72133
0.8298	Intermediate Similarity	NPC222613
0.8298	Intermediate Similarity	NPC474778
0.8298	Intermediate Similarity	NPC118648
0.8298	Intermediate Similarity	NPC31564
0.8298	Intermediate Similarity	NPC474732
0.8298	Intermediate Similarity	NPC474733
0.8265	Intermediate Similarity	NPC166906
0.8257	Intermediate Similarity	NPC474518
0.8252	Intermediate Similarity	NPC137657
0.8247	Intermediate Similarity	NPC168027
0.8247	Intermediate Similarity	NPC475806
0.8247	Intermediate Similarity	NPC63748
0.8247	Intermediate Similarity	NPC185936
0.8235	Intermediate Similarity	NPC136289
0.8235	Intermediate Similarity	NPC473424
0.8229	Intermediate Similarity	NPC186688
0.8229	Intermediate Similarity	NPC31985
0.8229	Intermediate Similarity	NPC1015
0.8224	Intermediate Similarity	NPC71348
0.8218	Intermediate Similarity	NPC144956
0.8218	Intermediate Similarity	NPC316964
0.8211	Intermediate Similarity	NPC141292
0.8208	Intermediate Similarity	NPC76084
0.82	Intermediate Similarity	NPC108078
0.8191	Intermediate Similarity	NPC470574
0.8191	Intermediate Similarity	NPC469948
0.8182	Intermediate Similarity	NPC473170
0.8182	Intermediate Similarity	NPC271195
0.8172	Intermediate Similarity	NPC64600
0.8165	Intermediate Similarity	NPC270929
0.8163	Intermediate Similarity	NPC474807
0.8163	Intermediate Similarity	NPC12722
0.8155	Intermediate Similarity	NPC264048
0.8155	Intermediate Similarity	NPC311612
0.8148	Intermediate Similarity	NPC122056
0.8144	Intermediate Similarity	NPC48010
0.8144	Intermediate Similarity	NPC85173
0.8144	Intermediate Similarity	NPC126993
0.8137	Intermediate Similarity	NPC81530
0.8131	Intermediate Similarity	NPC474229
0.8125	Intermediate Similarity	NPC471724
0.8125	Intermediate Similarity	NPC310752
0.8125	Intermediate Similarity	NPC474677
0.8125	Intermediate Similarity	NPC53911
0.8125	Intermediate Similarity	NPC292491
0.8119	Intermediate Similarity	NPC103051
0.8113	Intermediate Similarity	NPC214644
0.8113	Intermediate Similarity	NPC475941
0.8113	Intermediate Similarity	NPC474901
0.8108	Intermediate Similarity	NPC476960
0.81	Intermediate Similarity	NPC305483
0.81	Intermediate Similarity	NPC192428
0.81	Intermediate Similarity	NPC96859
0.81	Intermediate Similarity	NPC328162
0.81	Intermediate Similarity	NPC160056
0.8095	Intermediate Similarity	NPC44063
0.8095	Intermediate Similarity	NPC475294
0.8095	Intermediate Similarity	NPC185
0.8085	Intermediate Similarity	NPC221758
0.8085	Intermediate Similarity	NPC472265
0.8085	Intermediate Similarity	NPC473246
0.8085	Intermediate Similarity	NPC33913
0.8085	Intermediate Similarity	NPC214043
0.8085	Intermediate Similarity	NPC85774
0.8085	Intermediate Similarity	NPC59453
0.8081	Intermediate Similarity	NPC245972
0.8081	Intermediate Similarity	NPC471207
0.8081	Intermediate Similarity	NPC299100
0.8081	Intermediate Similarity	NPC8993
0.8081	Intermediate Similarity	NPC196485
0.8077	Intermediate Similarity	NPC235889
0.8061	Intermediate Similarity	NPC262870
0.8061	Intermediate Similarity	NPC472975
0.8058	Intermediate Similarity	NPC87351
0.8058	Intermediate Similarity	NPC477915
0.8056	Intermediate Similarity	NPC475970
0.8041	Intermediate Similarity	NPC473999
0.8041	Intermediate Similarity	NPC477943
0.8041	Intermediate Similarity	NPC474245
0.8041	Intermediate Similarity	NPC309603
0.8041	Intermediate Similarity	NPC472973
0.8041	Intermediate Similarity	NPC268406
0.8041	Intermediate Similarity	NPC26959
0.8041	Intermediate Similarity	NPC128496
0.8041	Intermediate Similarity	NPC32830
0.8039	Intermediate Similarity	NPC83709
0.8037	Intermediate Similarity	NPC239097
0.8037	Intermediate Similarity	NPC197428
0.8021	Intermediate Similarity	NPC136548
0.8021	Intermediate Similarity	NPC93778
0.802	Intermediate Similarity	NPC292133
0.802	Intermediate Similarity	NPC151488
0.802	Intermediate Similarity	NPC18509
0.8019	Intermediate Similarity	NPC469844
0.8019	Intermediate Similarity	NPC177064
0.8018	Intermediate Similarity	NPC329736
0.8018	Intermediate Similarity	NPC118638
0.8	Intermediate Similarity	NPC60681
0.8	Intermediate Similarity	NPC180950
0.8	Intermediate Similarity	NPC316215
0.8	Intermediate Similarity	NPC149047
0.8	Intermediate Similarity	NPC270958
0.8	Intermediate Similarity	NPC469599
0.8	Intermediate Similarity	NPC181265
0.8	Intermediate Similarity	NPC200702
0.7982	Intermediate Similarity	NPC317210
0.7981	Intermediate Similarity	NPC249187
0.7981	Intermediate Similarity	NPC470839
0.7981	Intermediate Similarity	NPC111323
0.7981	Intermediate Similarity	NPC247957
0.798	Intermediate Similarity	NPC79117
0.798	Intermediate Similarity	NPC474736
0.798	Intermediate Similarity	NPC475255
0.798	Intermediate Similarity	NPC472930
0.798	Intermediate Similarity	NPC470224
0.798	Intermediate Similarity	NPC477520
0.7963	Intermediate Similarity	NPC470960
0.7961	Intermediate Similarity	NPC476897
0.7959	Intermediate Similarity	NPC472325
0.7957	Intermediate Similarity	NPC136150
0.7946	Intermediate Similarity	NPC61520
0.7944	Intermediate Similarity	NPC258543
0.7944	Intermediate Similarity	NPC41405
0.7944	Intermediate Similarity	NPC2766
0.7944	Intermediate Similarity	NPC241927
0.7941	Intermediate Similarity	NPC477854
0.7938	Intermediate Similarity	NPC158778
0.7938	Intermediate Similarity	NPC193360
0.7938	Intermediate Similarity	NPC472802
0.7928	Intermediate Similarity	NPC470959
0.7928	Intermediate Similarity	NPC140055
0.7928	Intermediate Similarity	NPC167606
0.7928	Intermediate Similarity	NPC471854
0.7928	Intermediate Similarity	NPC286528
0.7928	Intermediate Similarity	NPC20302
0.7928	Intermediate Similarity	NPC476965
0.7925	Intermediate Similarity	NPC220229
0.7925	Intermediate Similarity	NPC475060
0.7921	Intermediate Similarity	NPC117133
0.7921	Intermediate Similarity	NPC95565
0.7921	Intermediate Similarity	NPC328371
0.7921	Intermediate Similarity	NPC471463
0.7917	Intermediate Similarity	NPC94755
0.7917	Intermediate Similarity	NPC183736
0.7917	Intermediate Similarity	NPC51014
0.7905	Intermediate Similarity	NPC209502
0.7905	Intermediate Similarity	NPC118911
0.7905	Intermediate Similarity	NPC255309
0.7905	Intermediate Similarity	NPC204833
0.7905	Intermediate Similarity	NPC72255
0.7905	Intermediate Similarity	NPC96268
0.79	Intermediate Similarity	NPC111015
0.79	Intermediate Similarity	NPC292793
0.79	Intermediate Similarity	NPC472976
0.79	Intermediate Similarity	NPC472977
0.79	Intermediate Similarity	NPC67831
0.79	Intermediate Similarity	NPC174051
0.79	Intermediate Similarity	NPC103527
0.79	Intermediate Similarity	NPC474690
0.7895	Intermediate Similarity	NPC470812
0.7895	Intermediate Similarity	NPC251170
0.7895	Intermediate Similarity	NPC146683
0.789	Intermediate Similarity	NPC234042
0.789	Intermediate Similarity	NPC152117
0.789	Intermediate Similarity	NPC475524
0.789	Intermediate Similarity	NPC100267
0.7885	Intermediate Similarity	NPC185530
0.7885	Intermediate Similarity	NPC308726
0.7885	Intermediate Similarity	NPC119601

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 NPC112167 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1603
0.2-0.3	4078
0.3-0.4	2252
0.4-0.5	602
0.5-0.6	177
0.6-0.7	142
0.7-0.8	121
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.883	High Similarity	NPD6079	Approved
0.8617	High Similarity	NPD5328	Approved
0.8298	Intermediate Similarity	NPD3618	Phase 1
0.8283	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8283	Intermediate Similarity	NPD5222	Approved
0.8283	Intermediate Similarity	NPD5221	Approved
0.8218	Intermediate Similarity	NPD4696	Approved
0.8218	Intermediate Similarity	NPD5286	Approved
0.8218	Intermediate Similarity	NPD5285	Approved
0.82	Intermediate Similarity	NPD5173	Approved
0.819	Intermediate Similarity	NPD6899	Approved
0.819	Intermediate Similarity	NPD6881	Approved
0.8137	Intermediate Similarity	NPD5223	Approved
0.8131	Intermediate Similarity	NPD6649	Approved
0.8131	Intermediate Similarity	NPD6650	Approved
0.81	Intermediate Similarity	NPD4697	Phase 3
0.8095	Intermediate Similarity	NPD5697	Approved
0.8085	Intermediate Similarity	NPD4786	Approved
0.8058	Intermediate Similarity	NPD4633	Approved
0.8058	Intermediate Similarity	NPD5211	Phase 2
0.8058	Intermediate Similarity	NPD5226	Approved
0.8058	Intermediate Similarity	NPD5225	Approved
0.8058	Intermediate Similarity	NPD5224	Approved
0.8037	Intermediate Similarity	NPD7290	Approved
0.8037	Intermediate Similarity	NPD7102	Approved
0.8037	Intermediate Similarity	NPD6883	Approved
0.802	Intermediate Similarity	NPD4755	Approved
0.8019	Intermediate Similarity	NPD6011	Approved
0.8	Intermediate Similarity	NPD6402	Approved
0.8	Intermediate Similarity	NPD6675	Approved
0.8	Intermediate Similarity	NPD5739	Approved
0.8	Intermediate Similarity	NPD7128	Approved
0.7981	Intermediate Similarity	NPD5174	Approved
0.7981	Intermediate Similarity	NPD5175	Approved
0.798	Intermediate Similarity	NPD4202	Approved
0.7963	Intermediate Similarity	NPD8130	Phase 1
0.7963	Intermediate Similarity	NPD6617	Approved
0.7963	Intermediate Similarity	NPD6869	Approved
0.7963	Intermediate Similarity	NPD6847	Approved
0.7944	Intermediate Similarity	NPD6012	Approved
0.7944	Intermediate Similarity	NPD6373	Approved
0.7944	Intermediate Similarity	NPD6372	Approved
0.7944	Intermediate Similarity	NPD6014	Approved
0.7944	Intermediate Similarity	NPD6013	Approved
0.7928	Intermediate Similarity	NPD7115	Discovery
0.7905	Intermediate Similarity	NPD5141	Approved
0.789	Intermediate Similarity	NPD6882	Approved
0.789	Intermediate Similarity	NPD8297	Approved
0.7872	Intermediate Similarity	NPD3667	Approved
0.7864	Intermediate Similarity	NPD4700	Approved
0.785	Intermediate Similarity	NPD7320	Approved
0.783	Intermediate Similarity	NPD6008	Approved
0.78	Intermediate Similarity	NPD6399	Phase 3
0.7757	Intermediate Similarity	NPD5701	Approved
0.7708	Intermediate Similarity	NPD3665	Phase 1
0.7708	Intermediate Similarity	NPD3133	Approved
0.7708	Intermediate Similarity	NPD3666	Approved
0.7685	Intermediate Similarity	NPD4729	Approved
0.7685	Intermediate Similarity	NPD4730	Approved
0.7647	Intermediate Similarity	NPD4629	Approved
0.7647	Intermediate Similarity	NPD5210	Approved
0.7642	Intermediate Similarity	NPD4754	Approved
0.7636	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5690	Phase 2
0.7551	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5279	Phase 3
0.7545	Intermediate Similarity	NPD5169	Approved
0.7545	Intermediate Similarity	NPD5250	Approved
0.7545	Intermediate Similarity	NPD5248	Approved
0.7545	Intermediate Similarity	NPD5251	Approved
0.7545	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5247	Approved
0.7545	Intermediate Similarity	NPD4634	Approved
0.7545	Intermediate Similarity	NPD5135	Approved
0.7545	Intermediate Similarity	NPD5249	Phase 3
0.7544	Intermediate Similarity	NPD6335	Approved
0.7523	Intermediate Similarity	NPD5168	Approved
0.7523	Intermediate Similarity	NPD5128	Approved
0.7522	Intermediate Similarity	NPD6868	Approved
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD4753	Phase 2
0.75	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD4221	Approved
0.75	Intermediate Similarity	NPD6084	Phase 2
0.75	Intermediate Similarity	NPD4223	Phase 3
0.75	Intermediate Similarity	NPD4768	Approved
0.75	Intermediate Similarity	NPD4767	Approved
0.7478	Intermediate Similarity	NPD7101	Approved
0.7478	Intermediate Similarity	NPD7100	Approved
0.7477	Intermediate Similarity	NPD5217	Approved
0.7477	Intermediate Similarity	NPD5216	Approved
0.7477	Intermediate Similarity	NPD5215	Approved
0.7477	Intermediate Similarity	NPD5127	Approved
0.7476	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD3573	Approved
0.7456	Intermediate Similarity	NPD6317	Approved
0.7449	Intermediate Similarity	NPD5329	Approved
0.7414	Intermediate Similarity	NPD6054	Approved
0.7391	Intermediate Similarity	NPD6314	Approved
0.7391	Intermediate Similarity	NPD6313	Approved
0.7379	Intermediate Similarity	NPD7748	Approved
0.7374	Intermediate Similarity	NPD6409	Approved
0.7374	Intermediate Similarity	NPD7146	Approved
0.7374	Intermediate Similarity	NPD6684	Approved
0.7374	Intermediate Similarity	NPD7521	Approved
0.7374	Intermediate Similarity	NPD7334	Approved
0.7374	Intermediate Similarity	NPD5330	Approved
0.7373	Intermediate Similarity	NPD7604	Phase 2
0.7368	Intermediate Similarity	NPD6274	Approved
0.7353	Intermediate Similarity	NPD7515	Phase 2
0.735	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4197	Approved
0.7333	Intermediate Similarity	NPD7902	Approved
0.7308	Intermediate Similarity	NPD5695	Phase 3
0.7304	Intermediate Similarity	NPD6009	Approved
0.7288	Intermediate Similarity	NPD6370	Approved
0.7281	Intermediate Similarity	NPD5167	Approved
0.7265	Intermediate Similarity	NPD6319	Approved
0.7264	Intermediate Similarity	NPD5696	Approved
0.7245	Intermediate Similarity	NPD4788	Approved
0.7228	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6672	Approved
0.7228	Intermediate Similarity	NPD6903	Approved
0.7228	Intermediate Similarity	NPD5737	Approved
0.7212	Intermediate Similarity	NPD6001	Approved
0.7203	Intermediate Similarity	NPD6015	Approved
0.7203	Intermediate Similarity	NPD5983	Phase 2
0.7203	Intermediate Similarity	NPD6016	Approved
0.72	Intermediate Similarity	NPD4693	Phase 3
0.72	Intermediate Similarity	NPD4690	Approved
0.72	Intermediate Similarity	NPD4689	Approved
0.72	Intermediate Similarity	NPD5205	Approved
0.72	Intermediate Similarity	NPD4688	Approved
0.72	Intermediate Similarity	NPD4138	Approved
0.72	Intermediate Similarity	NPD5280	Approved
0.72	Intermediate Similarity	NPD4694	Approved
0.7188	Intermediate Similarity	NPD4195	Approved
0.7184	Intermediate Similarity	NPD5284	Approved
0.7184	Intermediate Similarity	NPD5281	Approved
0.7172	Intermediate Similarity	NPD3668	Phase 3
0.7167	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD5988	Approved
0.7128	Intermediate Similarity	NPD7339	Approved
0.7128	Intermediate Similarity	NPD6942	Approved
0.7119	Intermediate Similarity	NPD6059	Approved
0.7113	Intermediate Similarity	NPD7525	Registered
0.7107	Intermediate Similarity	NPD6616	Approved
0.7107	Intermediate Similarity	NPD6336	Discontinued
0.7103	Intermediate Similarity	NPD7638	Approved
0.71	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD1694	Approved
0.7087	Intermediate Similarity	NPD5207	Approved
0.7059	Intermediate Similarity	NPD6908	Approved
0.7059	Intermediate Similarity	NPD6909	Approved
0.7049	Intermediate Similarity	NPD7078	Approved
0.7048	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7900	Approved
0.7037	Intermediate Similarity	NPD7639	Approved
0.7037	Intermediate Similarity	NPD7640	Approved
0.7019	Intermediate Similarity	NPD8035	Phase 2
0.7019	Intermediate Similarity	NPD6411	Approved
0.7019	Intermediate Similarity	NPD8034	Phase 2
0.6992	Remote Similarity	NPD7736	Approved
0.699	Remote Similarity	NPD6673	Approved
0.699	Remote Similarity	NPD6904	Approved
0.699	Remote Similarity	NPD6080	Approved
0.6939	Remote Similarity	NPD4695	Discontinued
0.6931	Remote Similarity	NPD1696	Phase 3
0.6907	Remote Similarity	NPD3617	Approved
0.6893	Remote Similarity	NPD5208	Approved
0.6893	Remote Similarity	NPD4518	Approved
0.6875	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4623	Approved
0.6863	Remote Similarity	NPD4519	Discontinued
0.6863	Remote Similarity	NPD6098	Approved
0.6857	Remote Similarity	NPD5694	Approved
0.6857	Remote Similarity	NPD6050	Approved
0.6842	Remote Similarity	NPD6924	Approved
0.6842	Remote Similarity	NPD6926	Approved
0.6827	Remote Similarity	NPD6101	Approved
0.6827	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6412	Phase 2
0.681	Remote Similarity	NPD6053	Discontinued
0.6792	Remote Similarity	NPD5133	Approved
0.6789	Remote Similarity	NPD5290	Discontinued
0.6789	Remote Similarity	NPD4225	Approved
0.6774	Remote Similarity	NPD8293	Discontinued
0.6768	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5692	Phase 3
0.6762	Remote Similarity	NPD4096	Approved
0.6762	Remote Similarity	NPD5785	Approved
0.6757	Remote Similarity	NPD5091	Approved
0.672	Remote Similarity	NPD6033	Approved
0.6702	Remote Similarity	NPD4747	Approved
0.6702	Remote Similarity	NPD4691	Approved
0.6701	Remote Similarity	NPD6933	Approved
0.67	Remote Similarity	NPD4692	Approved
0.67	Remote Similarity	NPD4139	Approved
0.67	Remote Similarity	NPD5369	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