NPASS Compound

Structure

NPC131118 OpenBabel07101718242D 24 25 0 0 0 0 0 0 0 0999 V2000 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 24 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 11 2 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 16 2 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 17 21 2 0 0 0 0 18 20 2 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.19
Volume:	362.575
LogP:	5.441
LogD:	4.2
LogS:	-4.4
# Rotatable Bonds:	7
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.719
Synthetic Accessibility Score:	2.344
Fsp3:	0.333
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:	-4.842
MDCK Permeability:	2.072891038551461e-05
Pgp-inhibitor:	0.951
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	99.1767807006836%
Volume Distribution (VD):	2.574
Pgp-substrate:	1.1633657217025757%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.788
CYP2C19-inhibitor:	0.966
CYP2C19-substrate:	0.123
CYP2C9-inhibitor:	0.842
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.965
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.715
CYP3A4-substrate:	0.328

ADMET: Excretion

Clearance (CL):	14.335
Half-life (T1/2):	0.701

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.269
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.567
Skin Sensitization:	0.943
Carcinogencity:	0.061
Eye Corrosion:	0.012
Eye Irritation:	0.935
Respiratory Toxicity:	0.171

Download Data

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

Natural Product: NPC131118

Natural Product ID:	NPC131118
*Common Name:**	1-(4-Hydroxy-2-Methoxyphenyl)-3-(4-Hydroxy-3-Prenylphenyl)Propane
IUPAC Name:	4-[3-(4-hydroxy-2-methoxyphenyl)propyl]-2-(3-methylbut-2-enyl)phenol
Synonyms:
Standard InCHIKey:	TXWULZGRVGVEDI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H26O3/c1-15(2)7-9-18-13-16(8-12-20(18)23)5-4-6-17-10-11-19(22)14-21(17)24-3/h7-8,10-14,22-23H,4-6,9H2,1-3H3
SMILES:	COc1cc(O)ccc1CCCc1ccc(c(c1)CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463254
PubChem CID:	10958364
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0003496] Cinnamylphenols

*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
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[11395279]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	n.a.	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	Shawnee National Forest, Harrisburg, IL, US	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12419367]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	leaves	Kaohsiung, Taiwan	2006-SEP	PMID[18986201]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[19296617]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	>	40.0	ug.mL-1	PMID[468523]

☑ 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 NPC131118 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	319
0.1-0.2	1712
0.2-0.3	4787
0.3-0.4	13770
0.4-0.5	4232
0.5-0.6	4817
0.6-0.7	7760
0.7-0.8	4256
0.8-0.85	738
0.85-0.9	236
0.9-0.95	63
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9818	High Similarity	NPC229147
0.9818	High Similarity	NPC54507
0.9818	High Similarity	NPC85292
0.9727	High Similarity	NPC464
0.9727	High Similarity	NPC185541
0.9649	High Similarity	NPC476633
0.9402	High Similarity	NPC246648
0.9402	High Similarity	NPC197351
0.9402	High Similarity	NPC86502
0.9402	High Similarity	NPC134195
0.9402	High Similarity	NPC106914
0.9381	High Similarity	NPC33270
0.9381	High Similarity	NPC474933
0.9381	High Similarity	NPC69261
0.9322	High Similarity	NPC103420
0.9322	High Similarity	NPC188022
0.9322	High Similarity	NPC17809
0.9322	High Similarity	NPC102540
0.9322	High Similarity	NPC285040
0.9322	High Similarity	NPC105031
0.9292	High Similarity	NPC150624
0.9292	High Similarity	NPC141090
0.9244	High Similarity	NPC276212
0.9231	High Similarity	NPC36016
0.9231	High Similarity	NPC100099
0.9224	High Similarity	NPC102639
0.9217	High Similarity	NPC184302
0.9204	High Similarity	NPC808
0.9204	High Similarity	NPC53906
0.9167	High Similarity	NPC149796
0.9153	High Similarity	NPC474160
0.9153	High Similarity	NPC76465
0.9153	High Similarity	NPC38761
0.9145	High Similarity	NPC54972
0.913	High Similarity	NPC190514
0.9123	High Similarity	NPC203113
0.9115	High Similarity	NPC22610
0.9115	High Similarity	NPC180508
0.9115	High Similarity	NPC228287
0.9115	High Similarity	NPC276737
0.9091	High Similarity	NPC274717
0.9091	High Similarity	NPC38664
0.9091	High Similarity	NPC61885
0.9091	High Similarity	NPC63698
0.9091	High Similarity	NPC53986
0.9083	High Similarity	NPC170485
0.9076	High Similarity	NPC159132
0.9052	High Similarity	NPC295259
0.9043	High Similarity	NPC15860
0.9043	High Similarity	NPC221549
0.9043	High Similarity	NPC244816
0.9043	High Similarity	NPC50521
0.9043	High Similarity	NPC127894
0.9043	High Similarity	NPC470759
0.9043	High Similarity	NPC195466
0.9043	High Similarity	NPC219070
0.9027	High Similarity	NPC35344
0.9027	High Similarity	NPC141003
0.9016	High Similarity	NPC93962
0.9016	High Similarity	NPC134360
0.9	High Similarity	NPC113495
0.9	High Similarity	NPC105925
0.8974	High Similarity	NPC93398
0.8974	High Similarity	NPC258979
0.8974	High Similarity	NPC8283
0.8966	High Similarity	NPC74821
0.8957	High Similarity	NPC114064
0.8943	High Similarity	NPC254000
0.8938	High Similarity	NPC280606
0.8934	High Similarity	NPC215300
0.8934	High Similarity	NPC28765
0.8926	High Similarity	NPC283049
0.8926	High Similarity	NPC50315
0.8926	High Similarity	NPC230479
0.8926	High Similarity	NPC26879
0.8917	High Similarity	NPC138248
0.8917	High Similarity	NPC228503
0.8909	High Similarity	NPC113457
0.8908	High Similarity	NPC77789
0.8908	High Similarity	NPC18128
0.8871	High Similarity	NPC118114
0.8871	High Similarity	NPC476166
0.8871	High Similarity	NPC103799
0.8871	High Similarity	NPC17343
0.8871	High Similarity	NPC129106
0.8871	High Similarity	NPC280653
0.8871	High Similarity	NPC268917
0.8871	High Similarity	NPC236014
0.8871	High Similarity	NPC207892
0.8871	High Similarity	NPC150011
0.8871	High Similarity	NPC129784
0.8871	High Similarity	NPC164804
0.8871	High Similarity	NPC164574
0.8871	High Similarity	NPC15543
0.8871	High Similarity	NPC211413
0.8871	High Similarity	NPC300875
0.8871	High Similarity	NPC282508
0.8871	High Similarity	NPC196765
0.8871	High Similarity	NPC293203
0.8871	High Similarity	NPC206224
0.8871	High Similarity	NPC118683
0.8871	High Similarity	NPC12875
0.8871	High Similarity	NPC244888
0.8871	High Similarity	NPC228369
0.8871	High Similarity	NPC68205
0.887	High Similarity	NPC167934
0.8852	High Similarity	NPC53781
0.8852	High Similarity	NPC236791
0.8852	High Similarity	NPC293054
0.8852	High Similarity	NPC82679
0.8852	High Similarity	NPC324112
0.8852	High Similarity	NPC74817
0.8852	High Similarity	NPC246620
0.8852	High Similarity	NPC473221
0.8852	High Similarity	NPC159968
0.8852	High Similarity	NPC124452
0.8852	High Similarity	NPC252131
0.8852	High Similarity	NPC282000
0.8852	High Similarity	NPC169474
0.885	High Similarity	NPC4493
0.885	High Similarity	NPC476632
0.885	High Similarity	NPC296920
0.885	High Similarity	NPC225679
0.885	High Similarity	NPC165770
0.885	High Similarity	NPC90520
0.8843	High Similarity	NPC278955
0.8843	High Similarity	NPC105718
0.8843	High Similarity	NPC234400
0.8843	High Similarity	NPC60885
0.8833	High Similarity	NPC282496
0.8833	High Similarity	NPC233526
0.8833	High Similarity	NPC136319
0.8824	High Similarity	NPC193364
0.8818	High Similarity	NPC474839
0.88	High Similarity	NPC13005
0.879	High Similarity	NPC27187
0.879	High Similarity	NPC32463
0.879	High Similarity	NPC470225
0.878	High Similarity	NPC222572
0.878	High Similarity	NPC38017
0.878	High Similarity	NPC87224
0.8772	High Similarity	NPC43525
0.877	High Similarity	NPC78974
0.877	High Similarity	NPC214406
0.877	High Similarity	NPC223953
0.877	High Similarity	NPC18924
0.877	High Similarity	NPC28730
0.877	High Similarity	NPC44748
0.877	High Similarity	NPC103823
0.877	High Similarity	NPC223136
0.877	High Similarity	NPC82299
0.8761	High Similarity	NPC2682
0.8761	High Similarity	NPC94045
0.8761	High Similarity	NPC168657
0.876	High Similarity	NPC270030
0.875	High Similarity	NPC150026
0.875	High Similarity	NPC57199
0.873	High Similarity	NPC85435
0.873	High Similarity	NPC77196
0.873	High Similarity	NPC92805
0.8729	High Similarity	NPC59561
0.8729	High Similarity	NPC172253
0.8727	High Similarity	NPC119860
0.872	High Similarity	NPC271945
0.872	High Similarity	NPC181497
0.871	High Similarity	NPC190144
0.871	High Similarity	NPC471518
0.871	High Similarity	NPC471519
0.8699	High Similarity	NPC243688
0.8699	High Similarity	NPC46978
0.8696	High Similarity	NPC117846
0.8689	High Similarity	NPC203133
0.8689	High Similarity	NPC81641
0.8689	High Similarity	NPC475169
0.8689	High Similarity	NPC17943
0.8689	High Similarity	NPC82483
0.8689	High Similarity	NPC472093
0.8689	High Similarity	NPC251855
0.8689	High Similarity	NPC298757
0.8689	High Similarity	NPC265483
0.8689	High Similarity	NPC233410
0.8689	High Similarity	NPC57490
0.8689	High Similarity	NPC116907
0.8689	High Similarity	NPC117214
0.8689	High Similarity	NPC299584
0.8689	High Similarity	NPC208950
0.8689	High Similarity	NPC221077
0.8689	High Similarity	NPC293801
0.8689	High Similarity	NPC193544
0.8673	High Similarity	NPC82016
0.8667	High Similarity	NPC97432
0.8667	High Similarity	NPC190454
0.8667	High Similarity	NPC75713
0.8661	High Similarity	NPC115335
0.8661	High Similarity	NPC225696
0.8661	High Similarity	NPC117048
0.8661	High Similarity	NPC223008
0.8661	High Similarity	NPC473107
0.8661	High Similarity	NPC97834
0.8661	High Similarity	NPC198154

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 NPC131118 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	1044
0.2-0.3	1455
0.3-0.4	2711
0.4-0.5	1800
0.5-0.6	1054
0.6-0.7	622
0.7-0.8	140
0.8-0.85	9
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8966	High Similarity	NPD1548	Phase 1
0.8943	High Similarity	NPD4907	Clinical (unspecified phase)
0.8824	High Similarity	NPD1610	Phase 2
0.878	High Similarity	NPD4908	Phase 1
0.856	High Similarity	NPD4625	Phase 3
0.8545	High Similarity	NPD940	Approved
0.8545	High Similarity	NPD846	Approved
0.8413	Intermediate Similarity	NPD3027	Phase 3
0.8361	Intermediate Similarity	NPD422	Phase 1
0.8226	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8226	Intermediate Similarity	NPD4749	Approved
0.8217	Intermediate Similarity	NPD1240	Approved
0.8203	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8189	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1607	Approved
0.8091	Intermediate Similarity	NPD2860	Approved
0.8091	Intermediate Similarity	NPD2859	Approved
0.8077	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1613	Approved
0.8062	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2934	Approved
0.8	Intermediate Similarity	NPD2933	Approved
0.7971	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD2861	Phase 2
0.7969	Intermediate Similarity	NPD3018	Phase 2
0.7965	Intermediate Similarity	NPD1242	Phase 1
0.7881	Intermediate Similarity	NPD5451	Approved
0.7881	Intermediate Similarity	NPD4750	Phase 3
0.7879	Intermediate Similarity	NPD5124	Phase 1
0.7879	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD3020	Approved
0.7836	Intermediate Similarity	NPD1510	Phase 2
0.7797	Intermediate Similarity	NPD2684	Approved
0.7795	Intermediate Similarity	NPD2983	Phase 2
0.7795	Intermediate Similarity	NPD2982	Phase 2
0.7787	Intermediate Similarity	NPD6671	Approved
0.7778	Intermediate Similarity	NPD968	Approved
0.777	Intermediate Similarity	NPD7213	Phase 3
0.777	Intermediate Similarity	NPD7212	Phase 2
0.776	Intermediate Similarity	NPD4626	Approved
0.7721	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD2981	Phase 2
0.7714	Intermediate Similarity	NPD7447	Phase 1
0.7714	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD4060	Phase 1
0.7664	Intermediate Similarity	NPD1549	Phase 2
0.7656	Intermediate Similarity	NPD6582	Phase 2
0.7656	Intermediate Similarity	NPD6583	Phase 3
0.7647	Intermediate Similarity	NPD2935	Discontinued
0.7623	Intermediate Similarity	NPD5283	Phase 1
0.7611	Intermediate Similarity	NPD1809	Phase 2
0.7603	Intermediate Similarity	NPD228	Approved
0.7597	Intermediate Similarity	NPD8651	Approved
0.7589	Intermediate Similarity	NPD845	Approved
0.7569	Intermediate Similarity	NPD4380	Phase 2
0.7563	Intermediate Similarity	NPD290	Approved
0.7559	Intermediate Similarity	NPD3847	Discontinued
0.7556	Intermediate Similarity	NPD4097	Suspended
0.7554	Intermediate Similarity	NPD3750	Approved
0.7541	Intermediate Similarity	NPD5535	Approved
0.7541	Intermediate Similarity	NPD7843	Approved
0.7538	Intermediate Similarity	NPD2797	Approved
0.7534	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6099	Approved
0.7518	Intermediate Similarity	NPD6100	Approved
0.7518	Intermediate Similarity	NPD2796	Approved
0.7517	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD6387	Discontinued
0.75	Intermediate Similarity	NPD1091	Approved
0.7483	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD6584	Phase 3
0.7481	Intermediate Similarity	NPD3690	Phase 2
0.7481	Intermediate Similarity	NPD3691	Phase 2
0.748	Intermediate Similarity	NPD2667	Approved
0.748	Intermediate Similarity	NPD2668	Approved
0.7462	Intermediate Similarity	NPD6696	Suspended
0.7432	Intermediate Similarity	NPD7768	Phase 2
0.7426	Intermediate Similarity	NPD6651	Approved
0.7407	Intermediate Similarity	NPD2238	Phase 2
0.7402	Intermediate Similarity	NPD1651	Approved
0.7402	Intermediate Similarity	NPD5691	Approved
0.7398	Intermediate Similarity	NPD821	Approved
0.7398	Intermediate Similarity	NPD1138	Approved
0.7385	Intermediate Similarity	NPD1669	Approved
0.7383	Intermediate Similarity	NPD7075	Discontinued
0.7372	Intermediate Similarity	NPD4538	Approved
0.7372	Intermediate Similarity	NPD4536	Approved
0.7372	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD2557	Approved
0.736	Intermediate Similarity	NPD7157	Approved
0.7344	Intermediate Similarity	NPD6516	Phase 2
0.7344	Intermediate Similarity	NPD5846	Approved
0.7338	Intermediate Similarity	NPD3540	Phase 1
0.7328	Intermediate Similarity	NPD3225	Approved
0.7328	Intermediate Similarity	NPD1283	Approved
0.7324	Intermediate Similarity	NPD6666	Approved
0.7324	Intermediate Similarity	NPD6667	Approved
0.7319	Intermediate Similarity	NPD7033	Discontinued
0.7317	Intermediate Similarity	NPD1139	Approved
0.7317	Intermediate Similarity	NPD1137	Approved
0.7308	Intermediate Similarity	NPD2233	Approved
0.7308	Intermediate Similarity	NPD2232	Approved
0.7308	Intermediate Similarity	NPD2230	Approved
0.7305	Intermediate Similarity	NPD3892	Phase 2
0.7305	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7466	Approved
0.7304	Intermediate Similarity	NPD844	Approved
0.7302	Intermediate Similarity	NPD3596	Phase 2
0.7299	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7819	Suspended
0.7295	Intermediate Similarity	NPD3021	Approved
0.7295	Intermediate Similarity	NPD3022	Approved
0.7286	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6799	Approved
0.7266	Intermediate Similarity	NPD3539	Phase 1
0.7266	Intermediate Similarity	NPD1551	Phase 2
0.7259	Intermediate Similarity	NPD6798	Discontinued
0.7259	Intermediate Similarity	NPD3268	Approved
0.7258	Intermediate Similarity	NPD7635	Approved
0.7252	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1652	Phase 2
0.723	Intermediate Similarity	NPD6801	Discontinued
0.723	Intermediate Similarity	NPD1934	Approved
0.7222	Intermediate Similarity	NPD709	Approved
0.7218	Intermediate Similarity	NPD4624	Approved
0.7206	Intermediate Similarity	NPD6405	Approved
0.7206	Intermediate Similarity	NPD6407	Approved
0.7194	Intermediate Similarity	NPD5960	Phase 3
0.7194	Intermediate Similarity	NPD3748	Approved
0.7194	Intermediate Similarity	NPD5588	Approved
0.719	Intermediate Similarity	NPD6232	Discontinued
0.719	Intermediate Similarity	NPD3134	Approved
0.7188	Intermediate Similarity	NPD1894	Discontinued
0.7188	Intermediate Similarity	NPD5303	Approved
0.7188	Intermediate Similarity	NPD5304	Approved
0.7188	Intermediate Similarity	NPD6581	Approved
0.7188	Intermediate Similarity	NPD6580	Approved
0.7183	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD111	Approved
0.7181	Intermediate Similarity	NPD2801	Approved
0.7177	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1608	Approved
0.7174	Intermediate Similarity	NPD3052	Approved
0.7174	Intermediate Similarity	NPD3054	Approved
0.7162	Intermediate Similarity	NPD6072	Discontinued
0.7153	Intermediate Similarity	NPD7041	Phase 2
0.7153	Intermediate Similarity	NPD1511	Approved
0.7153	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4476	Approved
0.7143	Intermediate Similarity	NPD4477	Approved
0.7132	Intermediate Similarity	NPD1296	Phase 2
0.7132	Intermediate Similarity	NPD3049	Approved
0.7132	Intermediate Similarity	NPD3443	Approved
0.7132	Intermediate Similarity	NPD3444	Approved
0.7132	Intermediate Similarity	NPD3445	Approved
0.7132	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD2342	Discontinued
0.7122	Intermediate Similarity	NPD2200	Suspended
0.7114	Intermediate Similarity	NPD37	Approved
0.7113	Intermediate Similarity	NPD2800	Approved
0.7103	Intermediate Similarity	NPD2533	Approved
0.7103	Intermediate Similarity	NPD2532	Approved
0.7103	Intermediate Similarity	NPD2534	Approved
0.7101	Intermediate Similarity	NPD6355	Discontinued
0.7099	Intermediate Similarity	NPD1535	Discovery
0.7099	Intermediate Similarity	NPD1281	Approved
0.7097	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6599	Discontinued
0.7094	Intermediate Similarity	NPD288	Approved
0.7086	Intermediate Similarity	NPD3882	Suspended
0.7083	Intermediate Similarity	NPD5058	Phase 3
0.708	Intermediate Similarity	NPD9295	Approved
0.7077	Intermediate Similarity	NPD4589	Approved
0.7077	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD1778	Approved
0.7071	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2799	Discontinued
0.7063	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1398	Phase 1
0.7063	Intermediate Similarity	NPD7003	Approved
0.7059	Intermediate Similarity	NPD3028	Approved
0.7059	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1512	Approved
0.7051	Intermediate Similarity	NPD7473	Discontinued
0.7045	Intermediate Similarity	NPD1481	Phase 2
0.7045	Intermediate Similarity	NPD3972	Approved
0.7042	Intermediate Similarity	NPD2424	Discontinued
0.7039	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4357	Discontinued
0.7031	Intermediate Similarity	NPD7340	Approved
0.7029	Intermediate Similarity	NPD3620	Phase 2

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