NPASS Compound

Structure

NPC13949 OpenBabel07101718222D 27 30 0 0 1 0 0 0 0 0999 V2000 -1.4576 2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3201 -2.6376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3709 0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2650 1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5630 1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0646 1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0976 -1.6627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5775 0.3600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2472 0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8709 1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0896 0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9195 -0.3930 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.0801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8307 -0.9825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7369 2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -1.3600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6634 1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1420 -1.3680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 12 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 7 1 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 21 1 0 0 0 0 10 15 1 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 23 2 0 0 0 0 12 27 1 0 0 0 0 13 6 1 1 0 0 0 13 19 1 0 0 0 0 14 21 1 1 0 0 0 14 22 1 0 0 0 0 15 20 1 0 0 0 0 15 21 1 1 0 0 0 16 20 1 0 0 0 0 16 24 2 0 0 0 0 17 22 1 1 0 0 0 17 25 1 0 0 0 0 18 26 2 0 0 0 0 19 22 1 6 0 0 0 19 27 1 0 0 0 0 21 5 1 1 0 0 0 22 18 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.21
Volume:	388.248
LogP:	1.724
LogD:	1.624
LogS:	-3.746
# Rotatable Bonds:	2
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.564
Synthetic Accessibility Score:	5.778
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.751
MDCK Permeability:	3.15E-05
Pgp-inhibitor:	0.759
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.18
30% Bioavailability (F30%):	0.719

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.912
Plasma Protein Binding (PPB):	53.54%
Volume Distribution (VD):	0.684
Pgp-substrate:	56.86%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.189
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.595
CYP2C9-inhibitor:	0.076
CYP2C9-substrate:	0.141
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.178
CYP3A4-inhibitor:	0.117
CYP3A4-substrate:	0.246

ADMET: Excretion

Clearance (CL):	4.781
Half-life (T1/2):	0.807

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.106
AMES Toxicity:	0.362
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.562
Carcinogencity:	0.492
Eye Corrosion:	0.036
Eye Irritation:	0.074
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: NPC13949

Natural Product ID:	NPC13949
*Common Name:**	Glaucocalyxin B
IUPAC Name:	n.a.
Synonyms:	Glaucocalyxin B
Standard InCHIKey:	LSUXOKVMORWDLT-KEXKRWMXSA-N
Standard InCHI:	InChI=1S/C22H30O5/c1-11-13-6-7-14-21(5)9-8-16(24)20(3,4)15(21)10-17(25)22(14,18(11)26)19(13)27-12(2)23/h13-15,17,19,25H,1,6-10H2,2-5H3/t13-,14-,15+,17+,19+,21-,22-/m0/s1
SMILES:	CC(=O)O[C@@H]1[C@H]2CC[C@@H]3[C@]1([C@H](O)C[C@H]1[C@@]3(C)CCC(=O)C1(C)C)C(=O)C2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL563681
PubChem CID:	14193399
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425589]
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[29286250]
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24459	Isodon pharicus	Species	Lamiaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2678	Cell Line	NB-4	Homo sapiens	IC50	=	7860.0	nM	PMID[516784]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6220.0	nM	PMID[516784]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	IC50	>	10000.0	nM	PMID[516784]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[516784]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[516784]

☑ 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 NPC13949 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	218
0.1-0.2	1594
0.2-0.3	5593
0.3-0.4	10572
0.4-0.5	10382
0.5-0.6	6081
0.6-0.7	5302
0.7-0.8	2509
0.8-0.85	262
0.85-0.9	93
0.9-0.95	76
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC210214
0.957	High Similarity	NPC52899
0.957	High Similarity	NPC163963
0.957	High Similarity	NPC289148
0.9551	High Similarity	NPC250753
0.9468	High Similarity	NPC148628
0.9468	High Similarity	NPC88203
0.9468	High Similarity	NPC286519
0.9468	High Similarity	NPC304832
0.9468	High Similarity	NPC76866
0.9468	High Similarity	NPC246736
0.9468	High Similarity	NPC214946
0.9462	High Similarity	NPC287676
0.9444	High Similarity	NPC294263
0.9438	High Similarity	NPC180849
0.9368	High Similarity	NPC470310
0.9368	High Similarity	NPC216114
0.9368	High Similarity	NPC87927
0.9355	High Similarity	NPC16911
0.9355	High Similarity	NPC78427
0.9271	High Similarity	NPC98603
0.9271	High Similarity	NPC84928
0.9239	High Similarity	NPC470232
0.9231	High Similarity	NPC144739
0.9231	High Similarity	NPC59170
0.9231	High Similarity	NPC59350
0.9231	High Similarity	NPC181594
0.9158	High Similarity	NPC471790
0.9158	High Similarity	NPC46848
0.9149	High Similarity	NPC471038
0.914	High Similarity	NPC329910
0.914	High Similarity	NPC104568
0.913	High Similarity	NPC153775
0.913	High Similarity	NPC475118
0.913	High Similarity	NPC111524
0.913	High Similarity	NPC101233
0.913	High Similarity	NPC261333
0.913	High Similarity	NPC470386
0.913	High Similarity	NPC91772
0.913	High Similarity	NPC104371
0.913	High Similarity	NPC29247
0.913	High Similarity	NPC289539
0.913	High Similarity	NPC129004
0.913	High Similarity	NPC470385
0.913	High Similarity	NPC215271
0.913	High Similarity	NPC292374
0.9121	High Similarity	NPC211403
0.9121	High Similarity	NPC299185
0.9121	High Similarity	NPC476168
0.9121	High Similarity	NPC198242
0.9101	High Similarity	NPC174619
0.9101	High Similarity	NPC165895
0.9072	High Similarity	NPC202793
0.9072	High Similarity	NPC474558
0.9062	High Similarity	NPC275990
0.9062	High Similarity	NPC309388
0.9062	High Similarity	NPC475803
0.9043	High Similarity	NPC10864
0.9032	High Similarity	NPC98639
0.9032	High Similarity	NPC84018
0.9032	High Similarity	NPC138245
0.9032	High Similarity	NPC29112
0.9032	High Similarity	NPC470229
0.9032	High Similarity	NPC231060
0.9011	High Similarity	NPC149761
0.9011	High Similarity	NPC80401
0.9011	High Similarity	NPC261994
0.9011	High Similarity	NPC470378
0.899	High Similarity	NPC231278
0.899	High Similarity	NPC112895
0.899	High Similarity	NPC218123
0.898	High Similarity	NPC265127
0.8969	High Similarity	NPC139347
0.8958	High Similarity	NPC148279
0.8947	High Similarity	NPC38296
0.8947	High Similarity	NPC162459
0.8947	High Similarity	NPC89099
0.8947	High Similarity	NPC474793
0.8947	High Similarity	NPC38471
0.8947	High Similarity	NPC28864
0.8947	High Similarity	NPC98837
0.8947	High Similarity	NPC20479
0.8936	High Similarity	NPC29410
0.8936	High Similarity	NPC140242
0.8936	High Similarity	NPC264979
0.8936	High Similarity	NPC470387
0.8936	High Similarity	NPC200054
0.8936	High Similarity	NPC135548
0.8925	High Similarity	NPC191094
0.8925	High Similarity	NPC47853
0.8925	High Similarity	NPC302008
0.8913	High Similarity	NPC278106
0.8878	High Similarity	NPC13149
0.8876	High Similarity	NPC102292
0.8854	High Similarity	NPC470388
0.8854	High Similarity	NPC293866
0.8817	High Similarity	NPC82138
0.8812	High Similarity	NPC471093
0.88	High Similarity	NPC273155
0.88	High Similarity	NPC211224
0.8788	High Similarity	NPC4115
0.8788	High Similarity	NPC12823
0.8788	High Similarity	NPC138908
0.8788	High Similarity	NPC37600
0.8788	High Similarity	NPC200957
0.8778	High Similarity	NPC471042
0.8776	High Similarity	NPC159442
0.8776	High Similarity	NPC96217
0.8776	High Similarity	NPC277074
0.8776	High Similarity	NPC209298
0.8776	High Similarity	NPC122811
0.8764	High Similarity	NPC146683
0.8763	High Similarity	NPC236585
0.875	High Similarity	NPC26270
0.8725	High Similarity	NPC29505
0.8725	High Similarity	NPC329953
0.8723	High Similarity	NPC64006
0.871	High Similarity	NPC470230
0.87	High Similarity	NPC176949
0.87	High Similarity	NPC201908
0.87	High Similarity	NPC166993
0.8687	High Similarity	NPC96268
0.8681	High Similarity	NPC259009
0.8681	High Similarity	NPC153604
0.866	High Similarity	NPC127408
0.866	High Similarity	NPC291785
0.866	High Similarity	NPC55503
0.866	High Similarity	NPC156324
0.866	High Similarity	NPC267921
0.8652	High Similarity	NPC291320
0.8652	High Similarity	NPC118800
0.8652	High Similarity	NPC471036
0.8632	High Similarity	NPC205173
0.8632	High Similarity	NPC266431
0.8617	High Similarity	NPC473690
0.8617	High Similarity	NPC471902
0.8617	High Similarity	NPC287118
0.8614	High Similarity	NPC63841
0.8614	High Similarity	NPC469733
0.8614	High Similarity	NPC55973
0.8614	High Similarity	NPC469729
0.86	High Similarity	NPC295366
0.8587	High Similarity	NPC56413
0.8571	High Similarity	NPC71706
0.8571	High Similarity	NPC60947
0.8571	High Similarity	NPC253886
0.8571	High Similarity	NPC121218
0.8571	High Similarity	NPC252614
0.8571	High Similarity	NPC14634
0.8571	High Similarity	NPC295276
0.8571	High Similarity	NPC81530
0.8558	High Similarity	NPC471252
0.8557	High Similarity	NPC288
0.8557	High Similarity	NPC109059
0.8544	High Similarity	NPC470281
0.8544	High Similarity	NPC213320
0.8542	High Similarity	NPC234564
0.8539	High Similarity	NPC110780
0.8529	High Similarity	NPC102741
0.8526	High Similarity	NPC169751
0.8526	High Similarity	NPC272635
0.8515	High Similarity	NPC88833
0.8515	High Similarity	NPC469746
0.8515	High Similarity	NPC67745
0.8515	High Similarity	NPC96333
0.8515	High Similarity	NPC186054
0.8515	High Similarity	NPC471461
0.8511	High Similarity	NPC471901
0.8511	High Similarity	NPC475416
0.85	High Similarity	NPC301787
0.85	High Similarity	NPC101842
0.8495	Intermediate Similarity	NPC57954
0.8495	Intermediate Similarity	NPC213832
0.8495	Intermediate Similarity	NPC471043
0.8485	Intermediate Similarity	NPC170615
0.8485	Intermediate Similarity	NPC136289
0.8478	Intermediate Similarity	NPC134197
0.8478	Intermediate Similarity	NPC472497
0.8469	Intermediate Similarity	NPC94906
0.8462	Intermediate Similarity	NPC473397
0.8462	Intermediate Similarity	NPC473352
0.8462	Intermediate Similarity	NPC190704
0.8462	Intermediate Similarity	NPC471034
0.8462	Intermediate Similarity	NPC474927
0.8454	Intermediate Similarity	NPC96839
0.8447	Intermediate Similarity	NPC473324
0.8444	Intermediate Similarity	NPC471037
0.8438	Intermediate Similarity	NPC288906
0.8438	Intermediate Similarity	NPC263135
0.8431	Intermediate Similarity	NPC232133
0.8431	Intermediate Similarity	NPC469984
0.8431	Intermediate Similarity	NPC189663
0.8431	Intermediate Similarity	NPC89860
0.8431	Intermediate Similarity	NPC471094
0.8431	Intermediate Similarity	NPC473410
0.8421	Intermediate Similarity	NPC244356
0.8421	Intermediate Similarity	NPC224060
0.8416	Intermediate Similarity	NPC222833
0.84	Intermediate Similarity	NPC469985
0.8387	Intermediate Similarity	NPC146937

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 NPC13949 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1954
0.2-0.3	3945
0.3-0.4	1997
0.4-0.5	559
0.5-0.6	213
0.6-0.7	139
0.7-0.8	135
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8155	Intermediate Similarity	NPD5697	Approved
0.8125	Intermediate Similarity	NPD8035	Phase 2
0.8125	Intermediate Similarity	NPD8034	Phase 2
0.8077	Intermediate Similarity	NPD6899	Approved
0.8077	Intermediate Similarity	NPD6881	Approved
0.8065	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD6675	Approved
0.8058	Intermediate Similarity	NPD6402	Approved
0.8058	Intermediate Similarity	NPD5739	Approved
0.8058	Intermediate Similarity	NPD7128	Approved
0.8019	Intermediate Similarity	NPD6650	Approved
0.8019	Intermediate Similarity	NPD6649	Approved
0.8	Intermediate Similarity	NPD6014	Approved
0.8	Intermediate Similarity	NPD6013	Approved
0.8	Intermediate Similarity	NPD6372	Approved
0.8	Intermediate Similarity	NPD6373	Approved
0.8	Intermediate Similarity	NPD6012	Approved
0.7981	Intermediate Similarity	NPD5701	Approved
0.7925	Intermediate Similarity	NPD6883	Approved
0.7925	Intermediate Similarity	NPD7290	Approved
0.7925	Intermediate Similarity	NPD7102	Approved
0.7905	Intermediate Similarity	NPD6011	Approved
0.7905	Intermediate Similarity	NPD7320	Approved
0.7857	Intermediate Similarity	NPD6399	Phase 3
0.785	Intermediate Similarity	NPD6617	Approved
0.785	Intermediate Similarity	NPD6869	Approved
0.785	Intermediate Similarity	NPD8130	Phase 1
0.785	Intermediate Similarity	NPD6847	Approved
0.7778	Intermediate Similarity	NPD6882	Approved
0.7778	Intermediate Similarity	NPD8297	Approved
0.7755	Intermediate Similarity	NPD6079	Approved
0.7745	Intermediate Similarity	NPD5286	Approved
0.7745	Intermediate Similarity	NPD4696	Approved
0.7745	Intermediate Similarity	NPD5285	Approved
0.7732	Intermediate Similarity	NPD5328	Approved
0.7723	Intermediate Similarity	NPD4755	Approved
0.766	Intermediate Similarity	NPD4788	Approved
0.7658	Intermediate Similarity	NPD7115	Discovery
0.7624	Intermediate Similarity	NPD5221	Approved
0.7624	Intermediate Similarity	NPD4697	Phase 3
0.7624	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5222	Approved
0.7611	Intermediate Similarity	NPD6319	Approved
0.7604	Intermediate Similarity	NPD3618	Phase 1
0.76	Intermediate Similarity	NPD7748	Approved
0.7596	Intermediate Similarity	NPD5224	Approved
0.7596	Intermediate Similarity	NPD4633	Approved
0.7596	Intermediate Similarity	NPD5226	Approved
0.7596	Intermediate Similarity	NPD5211	Phase 2
0.7596	Intermediate Similarity	NPD5225	Approved
0.7576	Intermediate Similarity	NPD7515	Phase 2
0.7573	Intermediate Similarity	NPD4700	Approved
0.7568	Intermediate Similarity	NPD6274	Approved
0.7549	Intermediate Similarity	NPD7902	Approved
0.7549	Intermediate Similarity	NPD6083	Phase 2
0.7549	Intermediate Similarity	NPD5173	Approved
0.7549	Intermediate Similarity	NPD6084	Phase 2
0.7547	Intermediate Similarity	NPD6008	Approved
0.7524	Intermediate Similarity	NPD5175	Approved
0.7524	Intermediate Similarity	NPD5174	Approved
0.7523	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5223	Approved
0.7476	Intermediate Similarity	NPD5696	Approved
0.7476	Intermediate Similarity	NPD4225	Approved
0.7473	Intermediate Similarity	NPD6117	Approved
0.7453	Intermediate Similarity	NPD5141	Approved
0.7431	Intermediate Similarity	NPD4634	Approved
0.7423	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6411	Approved
0.7396	Intermediate Similarity	NPD4786	Approved
0.7391	Intermediate Similarity	NPD6116	Phase 1
0.7387	Intermediate Similarity	NPD4632	Approved
0.7368	Intermediate Similarity	NPD3667	Approved
0.7368	Intermediate Similarity	NPD7100	Approved
0.7368	Intermediate Similarity	NPD7101	Approved
0.7353	Intermediate Similarity	NPD5695	Phase 3
0.735	Intermediate Similarity	NPD7492	Approved
0.7345	Intermediate Similarity	NPD6317	Approved
0.7327	Intermediate Similarity	NPD4202	Approved
0.7312	Intermediate Similarity	NPD6118	Approved
0.7312	Intermediate Similarity	NPD6115	Approved
0.7312	Intermediate Similarity	NPD6114	Approved
0.7312	Intermediate Similarity	NPD6697	Approved
0.7311	Intermediate Similarity	NPD7736	Approved
0.7308	Intermediate Similarity	NPD7638	Approved
0.7304	Intermediate Similarity	NPD6054	Approved
0.7288	Intermediate Similarity	NPD6616	Approved
0.7281	Intermediate Similarity	NPD6314	Approved
0.7281	Intermediate Similarity	NPD6335	Approved
0.7281	Intermediate Similarity	NPD6313	Approved
0.7273	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6868	Approved
0.7255	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7900	Approved
0.7253	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4730	Approved
0.7248	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4729	Approved
0.7248	Intermediate Similarity	NPD5128	Approved
0.7245	Intermediate Similarity	NPD7334	Approved
0.7245	Intermediate Similarity	NPD6684	Approved
0.7245	Intermediate Similarity	NPD7521	Approved
0.7245	Intermediate Similarity	NPD7146	Approved
0.7245	Intermediate Similarity	NPD6409	Approved
0.7245	Intermediate Similarity	NPD5330	Approved
0.7241	Intermediate Similarity	NPD6016	Approved
0.7241	Intermediate Similarity	NPD6015	Approved
0.7241	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7640	Approved
0.7238	Intermediate Similarity	NPD7639	Approved
0.7227	Intermediate Similarity	NPD7078	Approved
0.7222	Intermediate Similarity	NPD4768	Approved
0.7222	Intermediate Similarity	NPD4767	Approved
0.7216	Intermediate Similarity	NPD3665	Phase 1
0.7216	Intermediate Similarity	NPD3666	Approved
0.7216	Intermediate Similarity	NPD3133	Approved
0.72	Intermediate Similarity	NPD4753	Phase 2
0.72	Intermediate Similarity	NPD6101	Approved
0.72	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4754	Approved
0.7193	Intermediate Similarity	NPD6009	Approved
0.7184	Intermediate Similarity	NPD5210	Approved
0.7184	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4629	Approved
0.7179	Intermediate Similarity	NPD6370	Approved
0.7179	Intermediate Similarity	NPD5988	Approved
0.7174	Intermediate Similarity	NPD3703	Phase 2
0.7172	Intermediate Similarity	NPD3573	Approved
0.7155	Intermediate Similarity	NPD6059	Approved
0.7117	Intermediate Similarity	NPD5251	Approved
0.7117	Intermediate Similarity	NPD5249	Phase 3
0.7117	Intermediate Similarity	NPD5250	Approved
0.7117	Intermediate Similarity	NPD5247	Approved
0.7117	Intermediate Similarity	NPD5248	Approved
0.71	Intermediate Similarity	NPD6903	Approved
0.71	Intermediate Similarity	NPD6672	Approved
0.71	Intermediate Similarity	NPD5737	Approved
0.7094	Intermediate Similarity	NPD6909	Approved
0.7094	Intermediate Similarity	NPD5983	Phase 2
0.7094	Intermediate Similarity	NPD6908	Approved
0.7083	Intermediate Similarity	NPD8293	Discontinued
0.7054	Intermediate Similarity	NPD5217	Approved
0.7054	Intermediate Similarity	NPD5216	Approved
0.7054	Intermediate Similarity	NPD5215	Approved
0.7033	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3702	Approved
0.6975	Remote Similarity	NPD8328	Phase 3
0.6975	Remote Similarity	NPD7604	Phase 2
0.6967	Remote Similarity	NPD7319	Approved
0.6964	Remote Similarity	NPD5169	Approved
0.6964	Remote Similarity	NPD5135	Approved
0.6964	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5168	Approved
0.6923	Remote Similarity	NPD6001	Approved
0.6903	Remote Similarity	NPD5127	Approved
0.6897	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5284	Approved
0.6893	Remote Similarity	NPD5281	Approved
0.6869	Remote Similarity	NPD3668	Phase 3
0.6863	Remote Similarity	NPD6673	Approved
0.6863	Remote Similarity	NPD6904	Approved
0.6863	Remote Similarity	NPD6080	Approved
0.686	Remote Similarity	NPD7507	Approved
0.686	Remote Similarity	NPD6336	Discontinued
0.6854	Remote Similarity	NPD4224	Phase 2
0.6848	Remote Similarity	NPD5777	Approved
0.6837	Remote Similarity	NPD4223	Phase 3
0.6837	Remote Similarity	NPD4221	Approved
0.6827	Remote Similarity	NPD5779	Approved
0.6827	Remote Similarity	NPD5778	Approved
0.6813	Remote Similarity	NPD3698	Phase 2
0.6804	Remote Similarity	NPD7525	Registered
0.6796	Remote Similarity	NPD5785	Approved
0.6789	Remote Similarity	NPD7632	Discontinued
0.6783	Remote Similarity	NPD8133	Approved
0.6765	Remote Similarity	NPD5208	Approved
0.6739	Remote Similarity	NPD4244	Approved
0.6739	Remote Similarity	NPD4245	Approved
0.6735	Remote Similarity	NPD5369	Approved
0.6733	Remote Similarity	NPD6098	Approved
0.6733	Remote Similarity	NPD5786	Approved
0.6733	Remote Similarity	NPD5279	Phase 3
0.6731	Remote Similarity	NPD7637	Suspended
0.6731	Remote Similarity	NPD5693	Phase 1
0.6724	Remote Similarity	NPD5167	Approved
0.67	Remote Similarity	NPD4197	Approved
0.6696	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6081	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6435	Approved
0.6635	Remote Similarity	NPD5207	Approved
0.6635	Remote Similarity	NPD5692	Phase 3
0.6634	Remote Similarity	NPD1694	Approved
0.6634	Remote Similarity	NPD5329	Approved
0.6634	Remote Similarity	NPD5363	Approved
0.6633	Remote Similarity	NPD4695	Discontinued

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