NPASS Compound

Structure

NPC138502 OpenBabel07101719132D 22 25 0 0 1 0 0 0 0 0999 V2000 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3997 -1.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3998 -1.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 1.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 0.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 1.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7148 1.0829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5050 -0.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8653 0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0108 -0.7200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6397 -1.0707 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6182 0.3693 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2579 -0.7014 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8868 -1.0520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2471 0.0187 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 -0.6547 -2.0706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 6 1 1 0 0 0 14 16 1 0 0 0 0 14 21 1 6 0 0 0 15 19 1 6 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 6 0 0 0 17 20 1 1 0 0 0 17 22 1 0 0 0 0 19 4 1 6 0 0 0 20 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	387.2
Volume:	384.768
LogP:	4.227
LogD:	4.02
LogS:	-5.05
# Rotatable Bonds:	5
TPSA:	64.3
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.829
Synthetic Accessibility Score:	6.979
Fsp3:	0.727
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:	-5.113
MDCK Permeability:	3.207959889550693e-05
Pgp-inhibitor:	0.049
Pgp-substrate:	0.973
Human Intestinal Absorption (HIA):	0.065
20% Bioavailability (F20%):	0.899
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.773
Plasma Protein Binding (PPB):	87.8381118774414%
Volume Distribution (VD):	2.453
Pgp-substrate:	12.974359512329102%

ADMET: Metabolism

CYP1A2-inhibitor:	0.201
CYP1A2-substrate:	0.715
CYP2C19-inhibitor:	0.119
CYP2C19-substrate:	0.829
CYP2C9-inhibitor:	0.583
CYP2C9-substrate:	0.095
CYP2D6-inhibitor:	0.094
CYP2D6-substrate:	0.559
CYP3A4-inhibitor:	0.767
CYP3A4-substrate:	0.881

ADMET: Excretion

Clearance (CL):	14.337
Half-life (T1/2):	0.063

ADMET: Toxicity

hERG Blockers:	0.252
Human Hepatotoxicity (H-HT):	0.955
Drug-inuced Liver Injury (DILI):	0.895
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.942
Maximum Recommended Daily Dose:	0.841
Skin Sensitization:	0.384
Carcinogencity:	0.202
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC138502

Natural Product ID:	NPC138502
*Common Name:**	AZJIUNJISQOUNR-AYGHAXAXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AZJIUNJISQOUNR-AYGHAXAXSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-12-13-6-7-15-19(4)9-5-8-18(2,3)16(19)14(21)11-20(15,10-13)17(12)22/h13-17,21-22H,1,5-11H2,2-4H3/t13-,14+,15+,16-,17-,19+,20+/m1/s1
SMILES:	C=C1[C@@H]2CC[C@H]3[C@]4(C)CCCC(C)(C)[C@H]4[C@H](C[C@]3(C2)[C@@H]1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426523
PubChem CID:	n.a.
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
NPO20739	Jungermannia hyalina	Species	Jungermanniaceae	Eukaryota	n.a.	Guangxi Zhuang Autonomous Region, China	n.a.	PMID[25856683]
NPO20739	Jungermannia hyalina	Species	Jungermanniaceae	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	14

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[549635]
NPT2410	Cell Line	NCI-H1299	Homo sapiens	IC50	>	50000.0	nM	PMID[549635]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	50000.0	nM	PMID[549635]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[549635]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	50000.0	nM	PMID[549635]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	50000.0	nM	PMID[549635]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[549635]
NPT27	Others	Unspecified		IC50	>	50000.0	nM	PMID[549635]

☑ 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 NPC138502 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	166
0.1-0.2	1996
0.2-0.3	9288
0.3-0.4	15179
0.4-0.5	6005
0.5-0.6	5054
0.6-0.7	3697
0.7-0.8	1082
0.8-0.85	127
0.85-0.9	63
0.9-0.95	27
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC38141
0.9726	High Similarity	NPC24504
0.9722	High Similarity	NPC260301
0.9722	High Similarity	NPC307336
0.9595	High Similarity	NPC47149
0.9589	High Similarity	NPC472500
0.9589	High Similarity	NPC472499
0.9589	High Similarity	NPC472502
0.9589	High Similarity	NPC472501
0.9589	High Similarity	NPC475
0.9467	High Similarity	NPC157655
0.9459	High Similarity	NPC476316
0.9459	High Similarity	NPC5604
0.9444	High Similarity	NPC185536
0.9437	High Similarity	NPC472506
0.9324	High Similarity	NPC301707
0.9324	High Similarity	NPC477817
0.9324	High Similarity	NPC477819
0.9306	High Similarity	NPC476736
0.9296	High Similarity	NPC164045
0.9189	High Similarity	NPC331618
0.9189	High Similarity	NPC257191
0.9189	High Similarity	NPC212241
0.9189	High Similarity	NPC119355
0.9189	High Similarity	NPC248830
0.9178	High Similarity	NPC3403
0.9155	High Similarity	NPC45296
0.9103	High Similarity	NPC256567
0.9079	High Similarity	NPC78545
0.9079	High Similarity	NPC71535
0.9067	High Similarity	NPC42853
0.9067	High Similarity	NPC472342
0.9054	High Similarity	NPC14112
0.9054	High Similarity	NPC86305
0.9041	High Similarity	NPC308440
0.9041	High Similarity	NPC472503
0.9028	High Similarity	NPC111234
0.8947	High Similarity	NPC49599
0.8947	High Similarity	NPC49627
0.8919	High Similarity	NPC104387
0.8919	High Similarity	NPC231256
0.8919	High Similarity	NPC240235
0.8919	High Similarity	NPC178383
0.8919	High Similarity	NPC70982
0.8919	High Similarity	NPC230704
0.8919	High Similarity	NPC212879
0.8816	High Similarity	NPC167037
0.8816	High Similarity	NPC6978
0.8816	High Similarity	NPC138621
0.8816	High Similarity	NPC244385
0.88	High Similarity	NPC93662
0.88	High Similarity	NPC91573
0.88	High Similarity	NPC278091
0.88	High Similarity	NPC78067
0.8784	High Similarity	NPC145552
0.8784	High Similarity	NPC254509
0.8784	High Similarity	NPC25511
0.8784	High Similarity	NPC196358
0.8784	High Similarity	NPC192638
0.8784	High Similarity	NPC49168
0.8784	High Similarity	NPC62657
0.8784	High Similarity	NPC5046
0.8734	High Similarity	NPC110778
0.8734	High Similarity	NPC232023
0.8734	High Similarity	NPC477818
0.8701	High Similarity	NPC273410
0.8701	High Similarity	NPC1319
0.8701	High Similarity	NPC80530
0.8684	High Similarity	NPC202540
0.8667	High Similarity	NPC200243
0.8667	High Similarity	NPC144075
0.8659	High Similarity	NPC160304
0.8649	High Similarity	NPC195489
0.8642	High Similarity	NPC139724
0.8625	High Similarity	NPC255882
0.8608	High Similarity	NPC296701
0.8608	High Similarity	NPC218616
0.859	High Similarity	NPC102253
0.859	High Similarity	NPC475679
0.859	High Similarity	NPC322313
0.859	High Similarity	NPC236237
0.8571	High Similarity	NPC31828
0.8571	High Similarity	NPC285761
0.8571	High Similarity	NPC102708
0.8553	High Similarity	NPC237460
0.8537	High Similarity	NPC472495
0.85	High Similarity	NPC141941
0.85	High Similarity	NPC193870
0.8462	Intermediate Similarity	NPC30986
0.8462	Intermediate Similarity	NPC209430
0.8462	Intermediate Similarity	NPC116119
0.8462	Intermediate Similarity	NPC475727
0.8462	Intermediate Similarity	NPC472742
0.8462	Intermediate Similarity	NPC80297
0.8452	Intermediate Similarity	NPC53890
0.8452	Intermediate Similarity	NPC123252
0.8452	Intermediate Similarity	NPC219937
0.8452	Intermediate Similarity	NPC194485
0.8451	Intermediate Similarity	NPC27243
0.8451	Intermediate Similarity	NPC476737
0.8442	Intermediate Similarity	NPC470758
0.8442	Intermediate Similarity	NPC470711
0.8434	Intermediate Similarity	NPC471952
0.8421	Intermediate Similarity	NPC103822
0.8415	Intermediate Similarity	NPC201273
0.8415	Intermediate Similarity	NPC24277
0.8415	Intermediate Similarity	NPC121981
0.84	Intermediate Similarity	NPC211009
0.8395	Intermediate Similarity	NPC475798
0.8395	Intermediate Similarity	NPC127606
0.8395	Intermediate Similarity	NPC124172
0.8395	Intermediate Similarity	NPC209802
0.8354	Intermediate Similarity	NPC13554
0.8333	Intermediate Similarity	NPC85346
0.8333	Intermediate Similarity	NPC11908
0.8333	Intermediate Similarity	NPC302041
0.8333	Intermediate Similarity	NPC65897
0.8333	Intermediate Similarity	NPC44122
0.8333	Intermediate Similarity	NPC474216
0.8333	Intermediate Similarity	NPC477514
0.8333	Intermediate Similarity	NPC477522
0.8313	Intermediate Similarity	NPC470620
0.8313	Intermediate Similarity	NPC472497
0.8312	Intermediate Similarity	NPC73875
0.8312	Intermediate Similarity	NPC189883
0.8312	Intermediate Similarity	NPC470749
0.831	Intermediate Similarity	NPC68656
0.8293	Intermediate Similarity	NPC292553
0.8293	Intermediate Similarity	NPC318390
0.8289	Intermediate Similarity	NPC469593
0.8289	Intermediate Similarity	NPC469533
0.8289	Intermediate Similarity	NPC469534
0.8272	Intermediate Similarity	NPC216420
0.8272	Intermediate Similarity	NPC82623
0.8272	Intermediate Similarity	NPC85095
0.8272	Intermediate Similarity	NPC470929
0.8272	Intermediate Similarity	NPC207013
0.8272	Intermediate Similarity	NPC211135
0.8267	Intermediate Similarity	NPC301226
0.8256	Intermediate Similarity	NPC26046
0.8243	Intermediate Similarity	NPC477820
0.8243	Intermediate Similarity	NPC9942
0.8243	Intermediate Similarity	NPC210323
0.8235	Intermediate Similarity	NPC100313
0.8228	Intermediate Similarity	NPC28862
0.8228	Intermediate Similarity	NPC84694
0.8228	Intermediate Similarity	NPC47982
0.8228	Intermediate Similarity	NPC81306
0.8228	Intermediate Similarity	NPC109546
0.8228	Intermediate Similarity	NPC143182
0.8219	Intermediate Similarity	NPC185874
0.8219	Intermediate Similarity	NPC139207
0.8214	Intermediate Similarity	NPC67872
0.8205	Intermediate Similarity	NPC214570
0.8194	Intermediate Similarity	NPC60837
0.8194	Intermediate Similarity	NPC208198
0.8194	Intermediate Similarity	NPC282619
0.8194	Intermediate Similarity	NPC258595
0.8194	Intermediate Similarity	NPC11555
0.8194	Intermediate Similarity	NPC172613
0.8194	Intermediate Similarity	NPC2728
0.8193	Intermediate Similarity	NPC6605
0.8193	Intermediate Similarity	NPC472738
0.8193	Intermediate Similarity	NPC168231
0.8182	Intermediate Similarity	NPC121744
0.8182	Intermediate Similarity	NPC118508
0.8182	Intermediate Similarity	NPC322353
0.8182	Intermediate Similarity	NPC471723
0.8182	Intermediate Similarity	NPC257347
0.8182	Intermediate Similarity	NPC141071
0.8171	Intermediate Similarity	NPC263974
0.8171	Intermediate Similarity	NPC86238
0.8148	Intermediate Similarity	NPC470614
0.8148	Intermediate Similarity	NPC145143
0.8148	Intermediate Similarity	NPC1272
0.8148	Intermediate Similarity	NPC46881
0.8148	Intermediate Similarity	NPC20853
0.8148	Intermediate Similarity	NPC49964
0.8148	Intermediate Similarity	NPC202389
0.8148	Intermediate Similarity	NPC170985
0.8148	Intermediate Similarity	NPC477599
0.8148	Intermediate Similarity	NPC87489
0.8148	Intermediate Similarity	NPC101462
0.8148	Intermediate Similarity	NPC201852
0.8148	Intermediate Similarity	NPC472504
0.8148	Intermediate Similarity	NPC470049
0.814	Intermediate Similarity	NPC130840
0.8133	Intermediate Similarity	NPC232925
0.8133	Intermediate Similarity	NPC63588
0.8133	Intermediate Similarity	NPC251201
0.8125	Intermediate Similarity	NPC295131
0.8125	Intermediate Similarity	NPC26117
0.8125	Intermediate Similarity	NPC206735
0.8125	Intermediate Similarity	NPC234193
0.8125	Intermediate Similarity	NPC164840
0.8125	Intermediate Similarity	NPC241290
0.8125	Intermediate Similarity	NPC236112
0.8125	Intermediate Similarity	NPC209944
0.8118	Intermediate Similarity	NPC105495
0.8108	Intermediate Similarity	NPC276616

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 NPC138502 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	2334
0.2-0.3	4428
0.3-0.4	1569
0.4-0.5	271
0.5-0.6	159
0.6-0.7	172
0.7-0.8	55
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.859	High Similarity	NPD7525	Registered
0.8077	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD6942	Approved
0.7949	Intermediate Similarity	NPD7339	Approved
0.7857	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7645	Phase 2
0.7674	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4787	Phase 1
0.7619	Intermediate Similarity	NPD4788	Approved
0.7564	Intermediate Similarity	NPD4243	Approved
0.7532	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4748	Discontinued
0.7444	Intermediate Similarity	NPD4202	Approved
0.7375	Intermediate Similarity	NPD4785	Approved
0.7375	Intermediate Similarity	NPD6926	Approved
0.7375	Intermediate Similarity	NPD6924	Approved
0.7375	Intermediate Similarity	NPD4784	Approved
0.7349	Intermediate Similarity	NPD6929	Approved
0.7333	Intermediate Similarity	NPD8035	Phase 2
0.7333	Intermediate Similarity	NPD8034	Phase 2
0.7326	Intermediate Similarity	NPD4786	Approved
0.7303	Intermediate Similarity	NPD5328	Approved
0.7262	Intermediate Similarity	NPD6931	Approved
0.7262	Intermediate Similarity	NPD6930	Phase 2
0.7195	Intermediate Similarity	NPD6933	Approved
0.7188	Intermediate Similarity	NPD5211	Phase 2
0.7159	Intermediate Similarity	NPD3618	Phase 1
0.7158	Intermediate Similarity	NPD7640	Approved
0.7158	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD6079	Approved
0.7128	Intermediate Similarity	NPD4755	Approved
0.7126	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3133	Approved
0.7126	Intermediate Similarity	NPD3665	Phase 1
0.7126	Intermediate Similarity	NPD3666	Approved
0.7125	Intermediate Similarity	NPD7150	Approved
0.7125	Intermediate Similarity	NPD7152	Approved
0.7125	Intermediate Similarity	NPD7151	Approved
0.7125	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6925	Approved
0.7108	Intermediate Similarity	NPD5776	Phase 2
0.7108	Intermediate Similarity	NPD6116	Phase 1
0.7093	Intermediate Similarity	NPD3667	Approved
0.7089	Intermediate Similarity	NPD6923	Approved
0.7089	Intermediate Similarity	NPD6922	Approved
0.7073	Intermediate Similarity	NPD5275	Approved
0.7073	Intermediate Similarity	NPD4190	Phase 3
0.7059	Intermediate Similarity	NPD7509	Discontinued
0.7059	Intermediate Similarity	NPD6928	Phase 2
0.7053	Intermediate Similarity	NPD7638	Approved
0.7041	Intermediate Similarity	NPD5141	Approved
0.7024	Intermediate Similarity	NPD7145	Approved
0.7011	Intermediate Similarity	NPD6695	Phase 3
0.7	Intermediate Similarity	NPD7144	Approved
0.7	Intermediate Similarity	NPD4244	Approved
0.7	Intermediate Similarity	NPD7143	Approved
0.7	Intermediate Similarity	NPD4245	Approved
0.6988	Remote Similarity	NPD6117	Approved
0.6979	Remote Similarity	NPD5286	Approved
0.6979	Remote Similarity	NPD4700	Approved
0.6979	Remote Similarity	NPD5285	Approved
0.6979	Remote Similarity	NPD4696	Approved
0.6951	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4195	Approved
0.6907	Remote Similarity	NPD5223	Approved
0.6875	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3698	Phase 2
0.6875	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD8264	Approved
0.686	Remote Similarity	NPD7514	Phase 3
0.6854	Remote Similarity	NPD6893	Approved
0.6837	Remote Similarity	NPD5224	Approved
0.6837	Remote Similarity	NPD5225	Approved
0.6837	Remote Similarity	NPD5226	Approved
0.6837	Remote Similarity	NPD4633	Approved
0.6824	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6115	Approved
0.6824	Remote Similarity	NPD6114	Approved
0.6824	Remote Similarity	NPD6697	Approved
0.6824	Remote Similarity	NPD6118	Approved
0.68	Remote Similarity	NPD5739	Approved
0.68	Remote Similarity	NPD7128	Approved
0.68	Remote Similarity	NPD6402	Approved
0.68	Remote Similarity	NPD6675	Approved
0.6782	Remote Similarity	NPD6902	Approved
0.6774	Remote Similarity	NPD7515	Phase 2
0.6768	Remote Similarity	NPD5174	Approved
0.6768	Remote Similarity	NPD5175	Approved
0.6768	Remote Similarity	NPD4754	Approved
0.6739	Remote Similarity	NPD4753	Phase 2
0.6706	Remote Similarity	NPD6932	Approved
0.6705	Remote Similarity	NPD4223	Phase 3
0.6705	Remote Similarity	NPD4221	Approved
0.6703	Remote Similarity	NPD7750	Discontinued
0.6703	Remote Similarity	NPD7524	Approved
0.6702	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD3703	Phase 2
0.6667	Remote Similarity	NPD5221	Approved
0.6634	Remote Similarity	NPD4768	Approved
0.6634	Remote Similarity	NPD4767	Approved
0.6602	Remote Similarity	NPD6373	Approved
0.6602	Remote Similarity	NPD6372	Approved
0.6598	Remote Similarity	NPD5173	Approved
0.6591	Remote Similarity	NPD6898	Phase 1
0.6585	Remote Similarity	NPD4789	Approved
0.6569	Remote Similarity	NPD5697	Approved
0.6569	Remote Similarity	NPD5701	Approved
0.6559	Remote Similarity	NPD6051	Approved
0.6556	Remote Similarity	NPD4197	Approved
0.6552	Remote Similarity	NPD6683	Phase 2
0.6543	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5360	Phase 3
0.6538	Remote Similarity	NPD7102	Approved
0.6538	Remote Similarity	NPD6883	Approved
0.6538	Remote Similarity	NPD7290	Approved
0.6505	Remote Similarity	NPD4729	Approved
0.6505	Remote Similarity	NPD4730	Approved
0.6505	Remote Similarity	NPD5128	Approved
0.6505	Remote Similarity	NPD6011	Approved
0.6476	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6617	Approved
0.6476	Remote Similarity	NPD6650	Approved
0.6476	Remote Similarity	NPD6847	Approved
0.6476	Remote Similarity	NPD6649	Approved
0.6476	Remote Similarity	NPD6869	Approved
0.6476	Remote Similarity	NPD8130	Phase 1
0.6458	Remote Similarity	NPD7748	Approved
0.6452	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6013	Approved
0.6442	Remote Similarity	NPD6014	Approved
0.6442	Remote Similarity	NPD6012	Approved
0.6429	Remote Similarity	NPD7902	Approved
0.6429	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD6084	Phase 2
0.6422	Remote Similarity	NPD7327	Approved
0.6422	Remote Similarity	NPD7328	Approved
0.6421	Remote Similarity	NPD7087	Discontinued
0.6415	Remote Similarity	NPD6882	Approved
0.6415	Remote Similarity	NPD8297	Approved
0.6413	Remote Similarity	NPD6684	Approved
0.6413	Remote Similarity	NPD7146	Approved
0.6413	Remote Similarity	NPD4693	Phase 3
0.6413	Remote Similarity	NPD4689	Approved
0.6413	Remote Similarity	NPD4138	Approved
0.6413	Remote Similarity	NPD7521	Approved
0.6413	Remote Similarity	NPD7334	Approved
0.6413	Remote Similarity	NPD6409	Approved
0.6413	Remote Similarity	NPD5205	Approved
0.6413	Remote Similarity	NPD5279	Phase 3
0.6413	Remote Similarity	NPD4690	Approved
0.6413	Remote Similarity	NPD4688	Approved
0.6413	Remote Similarity	NPD5330	Approved
0.641	Remote Similarity	NPD368	Approved
0.64	Remote Similarity	NPD4159	Approved
0.6392	Remote Similarity	NPD5210	Approved
0.6392	Remote Similarity	NPD4629	Approved
0.6381	Remote Similarity	NPD4634	Approved
0.6381	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5135	Approved
0.6381	Remote Similarity	NPD5169	Approved
0.6381	Remote Similarity	NPD5247	Approved
0.6381	Remote Similarity	NPD5249	Phase 3
0.6381	Remote Similarity	NPD5248	Approved
0.6381	Remote Similarity	NPD5251	Approved
0.6381	Remote Similarity	NPD5250	Approved
0.6375	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD3668	Phase 3
0.6364	Remote Similarity	NPD7516	Approved
0.6364	Remote Similarity	NPD5290	Discontinued
0.6355	Remote Similarity	NPD8133	Approved
0.6321	Remote Similarity	NPD5216	Approved
0.6321	Remote Similarity	NPD5127	Approved
0.6321	Remote Similarity	NPD5217	Approved
0.6321	Remote Similarity	NPD5215	Approved
0.6306	Remote Similarity	NPD8294	Approved
0.6306	Remote Similarity	NPD8377	Approved
0.6277	Remote Similarity	NPD4723	Approved
0.6277	Remote Similarity	NPD4722	Approved
0.6277	Remote Similarity	NPD6903	Approved
0.625	Remote Similarity	NPD8378	Approved
0.625	Remote Similarity	NPD8379	Approved
0.625	Remote Similarity	NPD8296	Approved
0.625	Remote Similarity	NPD8380	Approved
0.625	Remote Similarity	NPD8033	Approved
0.625	Remote Similarity	NPD3671	Phase 1
0.625	Remote Similarity	NPD8335	Approved
0.6237	Remote Similarity	NPD4694	Approved
0.6237	Remote Similarity	NPD5690	Phase 2
0.6237	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD5280	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