NPASS Compound

Structure

CID102639 OpenBabel06191715452D 22 23 0 0 0 0 0 0 0 0999 V2000 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 6.0622 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 5.1962 2.0000 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 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 1.7321 -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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 0.8660 0.5000 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 0.8660 -2.5000 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 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 22 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 15 2 0 0 0 0 10 11 2 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 19 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 17 19 1 0 0 0 0 18 21 1 0 0 0 0 19 20 2 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.16
Volume:	333.852
LogP:	5.271
LogD:	4.298
LogS:	-5.134
# Rotatable Bonds:	5
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.615
Synthetic Accessibility Score:	2.426
Fsp3:	0.2
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:	-4.845
MDCK Permeability:	2.0253961338312365e-05
Pgp-inhibitor:	0.559
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.711
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.201
Plasma Protein Binding (PPB):	98.42382049560547%
Volume Distribution (VD):	3.313
Pgp-substrate:	1.610371708869934%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.676
CYP2C19-inhibitor:	0.971
CYP2C19-substrate:	0.204
CYP2C9-inhibitor:	0.86
CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.676
CYP2D6-substrate:	0.873
CYP3A4-inhibitor:	0.815
CYP3A4-substrate:	0.232

ADMET: Excretion

Clearance (CL):	12.663
Half-life (T1/2):	0.378

ADMET: Toxicity

hERG Blockers:	0.298
Human Hepatotoxicity (H-HT):	0.391
Drug-inuced Liver Injury (DILI):	0.378
AMES Toxicity:	0.137
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.372
Skin Sensitization:	0.87
Carcinogencity:	0.144
Eye Corrosion:	0.007
Eye Irritation:	0.745
Respiratory Toxicity:	0.265

Download Data

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

Natural Product: NPC102639

Natural Product ID:	NPC102639
*Common Name:**	Longistyline C
IUPAC Name:	3-methoxy-4-(3-methylbut-2-enyl)-5-[(E)-2-phenylethenyl]phenol
Synonyms:	Longistyline C
Standard InCHIKey:	NFAWEPOBHKEHPO-ZHACJKMWSA-N
Standard InCHI:	InChI=1S/C20H22O2/c1-15(2)9-12-19-17(13-18(21)14-20(19)22-3)11-10-16-7-5-4-6-8-16/h4-11,13-14,21H,12H2,1-3H3/b11-10+
SMILES:	COc1cc(O)cc(c1CC=C(C)C)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445702
PubChem CID:	6446720
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO27986	Lonchocarpus chiricanus	Species	Fabaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[11421729]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27806	Gossypium hirsutum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27806	Gossypium hirsutum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27619	Dianella laevis	Species	Hydrobiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27986	Lonchocarpus chiricanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27806	Gossypium hirsutum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27684	Stoebe plumosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27932	Schistocarpha bicolor	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4643	Cladophora prolifera	Species	Cladophoraceae	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
EC50	1
Others	3

Activity Type	# Activity
Organism	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1381	Organism	Aedes aegypti	Aedes aegypti	Activity	=	50.0	ppm	PMID[544211]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	2.2	n.a.	PMID[544212]
NPT2	Others	Unspecified		EC50	=	8370.0	nM	PMID[544212]
NPT2	Others	Unspecified		CC50	=	18540.0	nM	PMID[544212]

☑ 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 NPC102639 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	344
0.1-0.2	1776
0.2-0.3	4737
0.3-0.4	13461
0.4-0.5	4457
0.5-0.6	4289
0.6-0.7	7911
0.7-0.8	4562
0.8-0.85	784
0.85-0.9	306
0.9-0.95	64
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9576	High Similarity	NPC113495
0.9576	High Similarity	NPC105031
0.9496	High Similarity	NPC170485
0.9474	High Similarity	NPC69261
0.9474	High Similarity	NPC33270
0.9474	High Similarity	NPC474933
0.9469	High Similarity	NPC464
0.9469	High Similarity	NPC185541
0.9417	High Similarity	NPC473221
0.9402	High Similarity	NPC476633
0.9386	High Similarity	NPC150624
0.9386	High Similarity	NPC54507
0.9386	High Similarity	NPC229147
0.9386	High Similarity	NPC203113
0.9386	High Similarity	NPC141090
0.9386	High Similarity	NPC85292
0.9381	High Similarity	NPC180508
0.9381	High Similarity	NPC228287
0.9333	High Similarity	NPC82299
0.9328	High Similarity	NPC138248
0.9328	High Similarity	NPC228503
0.9322	High Similarity	NPC74137
0.931	High Similarity	NPC184302
0.9304	High Similarity	NPC244816
0.9304	High Similarity	NPC50521
0.9304	High Similarity	NPC195466
0.9304	High Similarity	NPC221549
0.9298	High Similarity	NPC53906
0.9298	High Similarity	NPC808
0.9262	High Similarity	NPC471519
0.9262	High Similarity	NPC471518
0.925	High Similarity	NPC105718
0.925	High Similarity	NPC278955
0.9224	High Similarity	NPC131118
0.9224	High Similarity	NPC190514
0.9211	High Similarity	NPC276737
0.9211	High Similarity	NPC22610
0.9204	High Similarity	NPC280606
0.9187	High Similarity	NPC126836
0.9187	High Similarity	NPC254000
0.918	High Similarity	NPC215300
0.9138	High Similarity	NPC219070
0.9138	High Similarity	NPC470759
0.9138	High Similarity	NPC127894
0.9138	High Similarity	NPC15860
0.913	High Similarity	NPC167934
0.9115	High Similarity	NPC296920
0.9115	High Similarity	NPC90520
0.9113	High Similarity	NPC282508
0.9113	High Similarity	NPC15543
0.9113	High Similarity	NPC473309
0.9098	High Similarity	NPC53781
0.9091	High Similarity	NPC234400
0.9091	High Similarity	NPC105925
0.9091	High Similarity	NPC60885
0.9052	High Similarity	NPC114064
0.9027	High Similarity	NPC94045
0.9024	High Similarity	NPC38017
0.9016	High Similarity	NPC78974
0.9016	High Similarity	NPC223953
0.9016	High Similarity	NPC223136
0.9016	High Similarity	NPC28730
0.9016	High Similarity	NPC18924
0.9016	High Similarity	NPC103823
0.9016	High Similarity	NPC214406
0.9016	High Similarity	NPC44748
0.9008	High Similarity	NPC270030
0.9	High Similarity	NPC18128
0.9	High Similarity	NPC57199
0.9	High Similarity	NPC77789
0.8968	High Similarity	NPC32778
0.8968	High Similarity	NPC469610
0.896	High Similarity	NPC8899
0.8952	High Similarity	NPC190144
0.8943	High Similarity	NPC124452
0.8943	High Similarity	NPC46978
0.8943	High Similarity	NPC324112
0.8943	High Similarity	NPC159968
0.8943	High Similarity	NPC236791
0.8943	High Similarity	NPC282000
0.8943	High Similarity	NPC74817
0.8943	High Similarity	NPC293054
0.8943	High Similarity	NPC82679
0.8943	High Similarity	NPC169474
0.8943	High Similarity	NPC246620
0.8938	High Similarity	NPC82016
0.8934	High Similarity	NPC265483
0.8934	High Similarity	NPC299584
0.8934	High Similarity	NPC82483
0.8934	High Similarity	NPC293801
0.8926	High Similarity	NPC282496
0.8926	High Similarity	NPC136319
0.8926	High Similarity	NPC233526
0.8926	High Similarity	NPC474160
0.8917	High Similarity	NPC75713
0.8898	High Similarity	NPC473107
0.8889	High Similarity	NPC469611
0.888	High Similarity	NPC192687
0.888	High Similarity	NPC224157
0.8879	High Similarity	NPC107240
0.8871	High Similarity	NPC154866
0.8862	High Similarity	NPC230479
0.8862	High Similarity	NPC50315
0.8862	High Similarity	NPC283049
0.8862	High Similarity	NPC26879
0.886	High Similarity	NPC168657
0.886	High Similarity	NPC2682
0.8843	High Similarity	NPC36016
0.8843	High Similarity	NPC100099
0.8833	High Similarity	NPC166759
0.8828	High Similarity	NPC258780
0.8828	High Similarity	NPC313081
0.8828	High Similarity	NPC10314
0.8828	High Similarity	NPC294884
0.8828	High Similarity	NPC200557
0.8828	High Similarity	NPC108198
0.8828	High Similarity	NPC37410
0.8828	High Similarity	NPC69029
0.8828	High Similarity	NPC158142
0.8824	High Similarity	NPC295259
0.881	High Similarity	NPC471517
0.881	High Similarity	NPC160623
0.881	High Similarity	NPC474356
0.881	High Similarity	NPC12275
0.881	High Similarity	NPC45715
0.88	High Similarity	NPC58164
0.88	High Similarity	NPC16577
0.88	High Similarity	NPC10225
0.879	High Similarity	NPC266555
0.879	High Similarity	NPC127587
0.878	High Similarity	NPC233410
0.878	High Similarity	NPC298757
0.878	High Similarity	NPC117214
0.878	High Similarity	NPC203133
0.878	High Similarity	NPC472093
0.878	High Similarity	NPC193544
0.878	High Similarity	NPC208950
0.878	High Similarity	NPC116907
0.878	High Similarity	NPC221077
0.878	High Similarity	NPC57490
0.878	High Similarity	NPC251855
0.878	High Similarity	NPC17943
0.878	High Similarity	NPC475169
0.8772	High Similarity	NPC202647
0.877	High Similarity	NPC76465
0.877	High Similarity	NPC95168
0.877	High Similarity	NPC38761
0.877	High Similarity	NPC84086
0.8761	High Similarity	NPC35543
0.876	High Similarity	NPC472649
0.876	High Similarity	NPC193364
0.876	High Similarity	NPC202846
0.876	High Similarity	NPC133463
0.876	High Similarity	NPC234952
0.876	High Similarity	NPC54972
0.876	High Similarity	NPC191462
0.876	High Similarity	NPC143139
0.876	High Similarity	NPC170328
0.876	High Similarity	NPC472647
0.876	High Similarity	NPC472648
0.876	High Similarity	NPC205442
0.876	High Similarity	NPC206525
0.875	High Similarity	NPC125649
0.875	High Similarity	NPC209199
0.875	High Similarity	NPC469659
0.875	High Similarity	NPC7515
0.875	High Similarity	NPC282255
0.875	High Similarity	NPC206737
0.875	High Similarity	NPC188378
0.875	High Similarity	NPC289258
0.875	High Similarity	NPC56764
0.875	High Similarity	NPC555
0.875	High Similarity	NPC276026
0.875	High Similarity	NPC474565
0.874	High Similarity	NPC6451
0.8739	High Similarity	NPC63010
0.8739	High Similarity	NPC74821
0.873	High Similarity	NPC51840
0.873	High Similarity	NPC299221
0.873	High Similarity	NPC234488
0.873	High Similarity	NPC311680
0.872	High Similarity	NPC53986
0.872	High Similarity	NPC28765
0.872	High Similarity	NPC38664
0.871	High Similarity	NPC76451
0.8699	High Similarity	NPC5796
0.8699	High Similarity	NPC134195
0.8699	High Similarity	NPC206487
0.8699	High Similarity	NPC86502
0.8699	High Similarity	NPC197351
0.8699	High Similarity	NPC246648
0.8699	High Similarity	NPC106914
0.8696	High Similarity	NPC303521
0.8692	High Similarity	NPC266006
0.8692	High Similarity	NPC71465
0.8692	High Similarity	NPC472646
0.8692	High Similarity	NPC56329
0.8692	High Similarity	NPC242715
0.8689	High Similarity	NPC473411
0.8689	High Similarity	NPC71579

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 NPC102639 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	1032
0.2-0.3	1485
0.3-0.4	2768
0.4-0.5	1704
0.5-0.6	989
0.6-0.7	678
0.7-0.8	143
0.8-0.85	13
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.88	High Similarity	NPD4625	Phase 3
0.876	High Similarity	NPD1610	Phase 2
0.8739	High Similarity	NPD1548	Phase 1
0.872	High Similarity	NPD4908	Phase 1
0.8583	High Similarity	NPD4907	Clinical (unspecified phase)
0.8504	High Similarity	NPD3027	Phase 3
0.8468	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8468	Intermediate Similarity	NPD4749	Approved
0.8413	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8281	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.823	Intermediate Similarity	NPD1242	Phase 1
0.8203	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8203	Intermediate Similarity	NPD3018	Phase 2
0.8203	Intermediate Similarity	NPD2861	Phase 2
0.8168	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD1613	Approved
0.816	Intermediate Similarity	NPD422	Phase 1
0.8158	Intermediate Similarity	NPD940	Approved
0.8158	Intermediate Similarity	NPD846	Approved
0.8154	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD4750	Phase 3
0.8031	Intermediate Similarity	NPD2982	Phase 2
0.8031	Intermediate Similarity	NPD2983	Phase 2
0.8015	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4626	Approved
0.7953	Intermediate Similarity	NPD2981	Phase 2
0.7895	Intermediate Similarity	NPD1240	Approved
0.7895	Intermediate Similarity	NPD4060	Phase 1
0.7886	Intermediate Similarity	NPD709	Approved
0.7886	Intermediate Similarity	NPD6671	Approved
0.7883	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD5283	Phase 1
0.7868	Intermediate Similarity	NPD6100	Approved
0.7868	Intermediate Similarity	NPD6099	Approved
0.7851	Intermediate Similarity	NPD228	Approved
0.7826	Intermediate Similarity	NPD3020	Approved
0.7788	Intermediate Similarity	NPD2934	Approved
0.7788	Intermediate Similarity	NPD2933	Approved
0.7778	Intermediate Similarity	NPD1607	Approved
0.7778	Intermediate Similarity	NPD4097	Suspended
0.777	Intermediate Similarity	NPD3750	Approved
0.777	Intermediate Similarity	NPD3892	Phase 2
0.7761	Intermediate Similarity	NPD2238	Phase 2
0.7719	Intermediate Similarity	NPD2859	Approved
0.7719	Intermediate Similarity	NPD2860	Approved
0.7698	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6696	Suspended
0.7674	Intermediate Similarity	NPD2233	Approved
0.7674	Intermediate Similarity	NPD2230	Approved
0.7674	Intermediate Similarity	NPD2232	Approved
0.7664	Intermediate Similarity	NPD1510	Phase 2
0.7638	Intermediate Similarity	NPD1651	Approved
0.7638	Intermediate Similarity	NPD5691	Approved
0.7615	Intermediate Similarity	NPD1669	Approved
0.7583	Intermediate Similarity	NPD968	Approved
0.7576	Intermediate Similarity	NPD4624	Approved
0.7576	Intermediate Similarity	NPD6584	Phase 3
0.7557	Intermediate Similarity	NPD1283	Approved
0.7554	Intermediate Similarity	NPD3540	Phase 1
0.7552	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD7447	Phase 1
0.7541	Intermediate Similarity	NPD3022	Approved
0.7541	Intermediate Similarity	NPD3021	Approved
0.7541	Intermediate Similarity	NPD5451	Approved
0.75	Intermediate Similarity	NPD7635	Approved
0.75	Intermediate Similarity	NPD7819	Suspended
0.7483	Intermediate Similarity	NPD7213	Phase 3
0.7483	Intermediate Similarity	NPD7212	Phase 2
0.7482	Intermediate Similarity	NPD3539	Phase 1
0.7482	Intermediate Similarity	NPD2935	Discontinued
0.7481	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD3705	Approved
0.7459	Intermediate Similarity	NPD2684	Approved
0.7442	Intermediate Similarity	NPD2668	Approved
0.7442	Intermediate Similarity	NPD2667	Approved
0.7432	Intermediate Similarity	NPD37	Approved
0.7429	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD844	Approved
0.741	Intermediate Similarity	NPD3748	Approved
0.7405	Intermediate Similarity	NPD1608	Approved
0.7394	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6232	Discontinued
0.7383	Intermediate Similarity	NPD2801	Approved
0.7383	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD290	Approved
0.7377	Intermediate Similarity	NPD2342	Discontinued
0.7376	Intermediate Similarity	NPD1549	Phase 2
0.7372	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3620	Phase 2
0.7368	Intermediate Similarity	NPD2797	Approved
0.7364	Intermediate Similarity	NPD3445	Approved
0.7364	Intermediate Similarity	NPD3443	Approved
0.7364	Intermediate Similarity	NPD3444	Approved
0.7361	Intermediate Similarity	NPD7041	Phase 2
0.7361	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1511	Approved
0.7357	Intermediate Similarity	NPD2796	Approved
0.735	Intermediate Similarity	NPD288	Approved
0.7348	Intermediate Similarity	NPD5327	Phase 3
0.7348	Intermediate Similarity	NPD6582	Phase 2
0.7348	Intermediate Similarity	NPD6583	Phase 3
0.7347	Intermediate Similarity	NPD4005	Discontinued
0.7328	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD1091	Approved
0.7328	Intermediate Similarity	NPD1281	Approved
0.7323	Intermediate Similarity	NPD7157	Approved
0.7319	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5124	Phase 1
0.7319	Intermediate Similarity	NPD5735	Approved
0.7315	Intermediate Similarity	NPD1934	Approved
0.7311	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2533	Approved
0.731	Intermediate Similarity	NPD2534	Approved
0.731	Intermediate Similarity	NPD2532	Approved
0.7308	Intermediate Similarity	NPD1778	Approved
0.7305	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6234	Discontinued
0.7302	Intermediate Similarity	NPD1398	Phase 1
0.7293	Intermediate Similarity	NPD8651	Approved
0.7287	Intermediate Similarity	NPD3091	Approved
0.7285	Intermediate Similarity	NPD3882	Suspended
0.7285	Intermediate Similarity	NPD4965	Approved
0.7285	Intermediate Similarity	NPD4967	Phase 2
0.7285	Intermediate Similarity	NPD4966	Approved
0.7273	Intermediate Similarity	NPD1840	Phase 2
0.7273	Intermediate Similarity	NPD7466	Approved
0.7266	Intermediate Similarity	NPD7340	Approved
0.726	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1512	Approved
0.7252	Intermediate Similarity	NPD3847	Discontinued
0.7252	Intermediate Similarity	NPD3496	Discontinued
0.7246	Intermediate Similarity	NPD4140	Approved
0.7246	Intermediate Similarity	NPD1558	Phase 1
0.7244	Intermediate Similarity	NPD7473	Discontinued
0.7241	Intermediate Similarity	NPD4357	Discontinued
0.7237	Intermediate Similarity	NPD4055	Discovery
0.7234	Intermediate Similarity	NPD1551	Phase 2
0.7222	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD821	Approved
0.7222	Intermediate Similarity	NPD2677	Approved
0.7222	Intermediate Similarity	NPD7843	Approved
0.7222	Intermediate Similarity	NPD5535	Approved
0.7219	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5536	Phase 2
0.7208	Intermediate Similarity	NPD6959	Discontinued
0.7208	Intermediate Similarity	NPD7199	Phase 2
0.7197	Intermediate Similarity	NPD3092	Approved
0.7197	Intermediate Similarity	NPD1611	Approved
0.7192	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD5763	Approved
0.7183	Intermediate Similarity	NPD5762	Approved
0.7181	Intermediate Similarity	NPD4380	Phase 2
0.7176	Intermediate Similarity	NPD17	Approved
0.7172	Intermediate Similarity	NPD7124	Phase 2
0.7171	Intermediate Similarity	NPD7768	Phase 2
0.7164	Intermediate Similarity	NPD3225	Approved
0.7163	Intermediate Similarity	NPD4108	Discontinued
0.7161	Intermediate Similarity	NPD7229	Phase 3
0.7153	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1024	Discontinued
0.7153	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD6353	Approved
0.7143	Intermediate Similarity	NPD2231	Phase 2
0.7143	Intermediate Similarity	NPD2157	Approved
0.7143	Intermediate Similarity	NPD2235	Phase 2
0.7143	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7037	Approved
0.7132	Intermediate Similarity	NPD1712	Approved
0.7123	Intermediate Similarity	NPD6799	Approved
0.7119	Intermediate Similarity	NPD1809	Phase 2
0.7115	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4476	Approved
0.7113	Intermediate Similarity	NPD4477	Approved
0.7111	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3094	Phase 2
0.7101	Intermediate Similarity	NPD5111	Phase 2
0.7101	Intermediate Similarity	NPD5110	Phase 2
0.7101	Intermediate Similarity	NPD3268	Approved
0.7101	Intermediate Similarity	NPD5109	Approved
0.7099	Intermediate Similarity	NPD5585	Approved
0.7099	Intermediate Similarity	NPD4093	Discontinued
0.7099	Intermediate Similarity	NPD1357	Approved
0.7094	Intermediate Similarity	NPD845	Approved
0.7092	Intermediate Similarity	NPD6111	Discontinued
0.7083	Intermediate Similarity	NPD3060	Approved
0.7083	Intermediate Similarity	NPD1652	Phase 2
0.708	Intermediate Similarity	NPD596	Approved
0.708	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD600	Approved
0.7075	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6355	Discontinued
0.7067	Intermediate Similarity	NPD4675	Approved
0.7067	Intermediate Similarity	NPD4678	Approved
0.7059	Intermediate Similarity	NPD3691	Phase 2
0.7059	Intermediate Similarity	NPD3690	Phase 2
0.7059	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6667	Approved
0.7055	Intermediate Similarity	NPD6666	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