NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.16
Volume:	275.214
LogP:	2.041
LogD:	2.287
LogS:	-2.583
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.736
Synthetic Accessibility Score:	5.193
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.643
MDCK Permeability:	1.7940310499398038e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.169
20% Bioavailability (F20%):	0.622
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.79
Plasma Protein Binding (PPB):	65.28791046142578%
Volume Distribution (VD):	1.442
Pgp-substrate:	25.1015625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.17
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.76
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.291
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.551
CYP3A4-inhibitor:	0.208
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	4.739
Half-life (T1/2):	0.278

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.005
Drug-inuced Liver Injury (DILI):	0.603
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.249
Maximum Recommended Daily Dose:	0.836
Skin Sensitization:	0.026
Carcinogencity:	0.67
Eye Corrosion:	0.003
Eye Irritation:	0.045
Respiratory Toxicity:	0.751

Download Data

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

Natural Product: NPC471560

Natural Product ID:	NPC471560
*Common Name:**	Cordiaquinol C
IUPAC Name:	(6S,7R)-7-ethenyl-7-methyl-6-prop-1-en-2-yl-4,5,6,8-tetrahydro-1H-naphthalene-1,4-diol
Synonyms:	Cordiaquinol C
Standard InCHIKey:	SQXTYAWGCAPKAP-LBDPXKHJSA-N
Standard InCHI:	InChI=1S/C16H22O2/c1-5-16(4)9-12-11(8-13(16)10(2)3)14(17)6-7-15(12)18/h5-7,13-15,17-18H,1-2,8-9H2,3-4H3/t13-,14?,15?,16-/m0/s1
SMILES:	CC(=C)C1CC2=C(CC1(C)C=C)C(C=CC2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL257133
PubChem CID:	44448124
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001661] Secondary alcohols

*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
NPO6865	Cordia fragrantissima	Species	Cordiaceae	Eukaryota	n.a.	Myanmar	n.a.	PMID[18088097]
NPO22854	Cordia globifera	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19368377]
NPO22854	Cordia globifera	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384317]
NPO6865	Cordia fragrantissima	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22854	Cordia globifera	Species	Cordiaceae	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	7
MIC	1

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	1.6	ug.mL-1	PMID[449336]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	6.9	ug.mL-1	PMID[449336]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	1.9	ug.mL-1	PMID[449336]
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	4.5	ug.mL-1	PMID[449335]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	25.0	ug.mL-1	PMID[449336]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.3	ug.mL-1	PMID[449336]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	20.0	ug.mL-1	PMID[449336]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.2	ug.mL-1	PMID[449336]

☑ 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 NPC471560 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	163
0.1-0.2	1337
0.2-0.3	7661
0.3-0.4	16173
0.4-0.5	9096
0.5-0.6	5636
0.6-0.7	2102
0.7-0.8	468
0.8-0.85	45
0.85-0.9	10
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9265	High Similarity	NPC130665
0.9254	High Similarity	NPC34834
0.8824	High Similarity	NPC474248
0.8806	High Similarity	NPC114651
0.875	High Similarity	NPC91594
0.8676	High Similarity	NPC96484
0.8657	High Similarity	NPC202017
0.863	High Similarity	NPC83351
0.863	High Similarity	NPC167891
0.8611	High Similarity	NPC253190
0.8611	High Similarity	NPC265588
0.8551	High Similarity	NPC473893
0.8529	High Similarity	NPC69649
0.8529	High Similarity	NPC171225
0.8529	High Similarity	NPC68703
0.8472	Intermediate Similarity	NPC69383
0.8472	Intermediate Similarity	NPC171148
0.8472	Intermediate Similarity	NPC313179
0.8462	Intermediate Similarity	NPC66020
0.8451	Intermediate Similarity	NPC471799
0.8421	Intermediate Similarity	NPC87489
0.8406	Intermediate Similarity	NPC208999
0.8406	Intermediate Similarity	NPC471238
0.84	Intermediate Similarity	NPC234193
0.8382	Intermediate Similarity	NPC267027
0.8382	Intermediate Similarity	NPC279434
0.8358	Intermediate Similarity	NPC96793
0.8358	Intermediate Similarity	NPC323424
0.8358	Intermediate Similarity	NPC107540
0.8356	Intermediate Similarity	NPC244488
0.8356	Intermediate Similarity	NPC247325
0.8333	Intermediate Similarity	NPC476366
0.8333	Intermediate Similarity	NPC306727
0.8333	Intermediate Similarity	NPC201048
0.8333	Intermediate Similarity	NPC471797
0.8312	Intermediate Similarity	NPC470384
0.831	Intermediate Similarity	NPC23954
0.831	Intermediate Similarity	NPC110799
0.831	Intermediate Similarity	NPC242001
0.8289	Intermediate Similarity	NPC476646
0.8289	Intermediate Similarity	NPC264245
0.8267	Intermediate Similarity	NPC30986
0.8267	Intermediate Similarity	NPC84694
0.8267	Intermediate Similarity	NPC47982
0.8267	Intermediate Similarity	NPC28862
0.8267	Intermediate Similarity	NPC81306
0.8267	Intermediate Similarity	NPC209430
0.8267	Intermediate Similarity	NPC109546
0.8267	Intermediate Similarity	NPC143182
0.8261	Intermediate Similarity	NPC197805
0.8243	Intermediate Similarity	NPC470711
0.8243	Intermediate Similarity	NPC470758
0.8235	Intermediate Similarity	NPC163678
0.8219	Intermediate Similarity	NPC32832
0.8209	Intermediate Similarity	NPC174956
0.8205	Intermediate Similarity	NPC231310
0.8205	Intermediate Similarity	NPC238485
0.8194	Intermediate Similarity	NPC182717
0.8194	Intermediate Similarity	NPC220939
0.8194	Intermediate Similarity	NPC474140
0.8194	Intermediate Similarity	NPC265485
0.8182	Intermediate Similarity	NPC202389
0.8182	Intermediate Similarity	NPC471408
0.8182	Intermediate Similarity	NPC50964
0.8182	Intermediate Similarity	NPC49964
0.8169	Intermediate Similarity	NPC92801
0.8169	Intermediate Similarity	NPC145498
0.8158	Intermediate Similarity	NPC96362
0.8158	Intermediate Similarity	NPC295131
0.8158	Intermediate Similarity	NPC164840
0.8158	Intermediate Similarity	NPC209944
0.8158	Intermediate Similarity	NPC241290
0.8143	Intermediate Similarity	NPC216460
0.8133	Intermediate Similarity	NPC474216
0.8133	Intermediate Similarity	NPC11908
0.8133	Intermediate Similarity	NPC476314
0.8125	Intermediate Similarity	NPC48891
0.8116	Intermediate Similarity	NPC222366
0.8116	Intermediate Similarity	NPC476039
0.8116	Intermediate Similarity	NPC326310
0.8116	Intermediate Similarity	NPC476406
0.8116	Intermediate Similarity	NPC286669
0.8108	Intermediate Similarity	NPC470749
0.8108	Intermediate Similarity	NPC470362
0.8088	Intermediate Similarity	NPC290367
0.8088	Intermediate Similarity	NPC300593
0.8088	Intermediate Similarity	NPC309300
0.8082	Intermediate Similarity	NPC91858
0.8082	Intermediate Similarity	NPC477138
0.8082	Intermediate Similarity	NPC243342
0.806	Intermediate Similarity	NPC321867
0.806	Intermediate Similarity	NPC207007
0.806	Intermediate Similarity	NPC68679
0.8056	Intermediate Similarity	NPC477792
0.8056	Intermediate Similarity	NPC471271
0.8056	Intermediate Similarity	NPC471272
0.8056	Intermediate Similarity	NPC471268
0.8056	Intermediate Similarity	NPC164022
0.8056	Intermediate Similarity	NPC167706
0.8052	Intermediate Similarity	NPC47761
0.8052	Intermediate Similarity	NPC6663
0.8052	Intermediate Similarity	NPC249423
0.8052	Intermediate Similarity	NPC209620
0.8052	Intermediate Similarity	NPC23852
0.803	Intermediate Similarity	NPC122239
0.8028	Intermediate Similarity	NPC9942
0.8026	Intermediate Similarity	NPC242767
0.8	Intermediate Similarity	NPC477791
0.8	Intermediate Similarity	NPC74995
0.8	Intermediate Similarity	NPC214570
0.8	Intermediate Similarity	NPC471798
0.7975	Intermediate Similarity	NPC205845
0.7973	Intermediate Similarity	NPC133580
0.7973	Intermediate Similarity	NPC291503
0.7971	Intermediate Similarity	NPC19569
0.7969	Intermediate Similarity	NPC148216
0.7969	Intermediate Similarity	NPC148163
0.7969	Intermediate Similarity	NPC130209
0.7949	Intermediate Similarity	NPC218616
0.7949	Intermediate Similarity	NPC296701
0.7949	Intermediate Similarity	NPC189972
0.7949	Intermediate Similarity	NPC101462
0.7945	Intermediate Similarity	NPC474743
0.7945	Intermediate Similarity	NPC68443
0.7941	Intermediate Similarity	NPC81615
0.7941	Intermediate Similarity	NPC474155
0.7941	Intermediate Similarity	NPC473759
0.791	Intermediate Similarity	NPC240506
0.7895	Intermediate Similarity	NPC275910
0.7895	Intermediate Similarity	NPC477514
0.7895	Intermediate Similarity	NPC473943
0.7887	Intermediate Similarity	NPC167527
0.7887	Intermediate Similarity	NPC32055
0.7887	Intermediate Similarity	NPC117804
0.7875	Intermediate Similarity	NPC274448
0.7875	Intermediate Similarity	NPC474083
0.7875	Intermediate Similarity	NPC109528
0.7867	Intermediate Similarity	NPC73875
0.7867	Intermediate Similarity	NPC134330
0.7867	Intermediate Similarity	NPC202642
0.7867	Intermediate Similarity	NPC46160
0.7867	Intermediate Similarity	NPC129165
0.7867	Intermediate Similarity	NPC113733
0.7867	Intermediate Similarity	NPC321016
0.7867	Intermediate Similarity	NPC96319
0.7867	Intermediate Similarity	NPC107059
0.7867	Intermediate Similarity	NPC321381
0.7867	Intermediate Similarity	NPC106432
0.7857	Intermediate Similarity	NPC149680
0.7848	Intermediate Similarity	NPC317458
0.7848	Intermediate Similarity	NPC474634
0.7848	Intermediate Similarity	NPC475789
0.7838	Intermediate Similarity	NPC469593
0.7838	Intermediate Similarity	NPC100334
0.7838	Intermediate Similarity	NPC469533
0.7838	Intermediate Similarity	NPC469534
0.7826	Intermediate Similarity	NPC225415
0.7826	Intermediate Similarity	NPC68656
0.7821	Intermediate Similarity	NPC474683
0.7821	Intermediate Similarity	NPC7505
0.7821	Intermediate Similarity	NPC474759
0.7821	Intermediate Similarity	NPC474752
0.7821	Intermediate Similarity	NPC474731
0.7821	Intermediate Similarity	NPC82986
0.7808	Intermediate Similarity	NPC95863
0.7808	Intermediate Similarity	NPC471662
0.7794	Intermediate Similarity	NPC225342
0.7794	Intermediate Similarity	NPC475251
0.7792	Intermediate Similarity	NPC233295
0.7792	Intermediate Similarity	NPC152061
0.7792	Intermediate Similarity	NPC308038
0.7778	Intermediate Similarity	NPC194417
0.7778	Intermediate Similarity	NPC261266
0.7778	Intermediate Similarity	NPC82979
0.7763	Intermediate Similarity	NPC130136
0.7763	Intermediate Similarity	NPC90979
0.7763	Intermediate Similarity	NPC477426
0.7763	Intermediate Similarity	NPC477425
0.7763	Intermediate Similarity	NPC472805
0.7763	Intermediate Similarity	NPC34177
0.7763	Intermediate Similarity	NPC157996
0.7763	Intermediate Similarity	NPC318495
0.7763	Intermediate Similarity	NPC155986
0.7763	Intermediate Similarity	NPC474826
0.7763	Intermediate Similarity	NPC198968
0.7763	Intermediate Similarity	NPC101475
0.7763	Intermediate Similarity	NPC40394
0.7763	Intermediate Similarity	NPC477427
0.7761	Intermediate Similarity	NPC475931
0.775	Intermediate Similarity	NPC185568
0.775	Intermediate Similarity	NPC83702
0.775	Intermediate Similarity	NPC470077
0.775	Intermediate Similarity	NPC474047
0.7746	Intermediate Similarity	NPC82337
0.7746	Intermediate Similarity	NPC136813
0.7733	Intermediate Similarity	NPC22105
0.7733	Intermediate Similarity	NPC304309
0.7733	Intermediate Similarity	NPC118508
0.7733	Intermediate Similarity	NPC134847
0.7733	Intermediate Similarity	NPC471723

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 NPC471560 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1984
0.2-0.3	4014
0.3-0.4	2107
0.4-0.5	580
0.5-0.6	223
0.6-0.7	86
0.7-0.8	4
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8472	Intermediate Similarity	NPD8264	Approved
0.806	Intermediate Similarity	NPD368	Approved
0.7969	Intermediate Similarity	NPD342	Phase 1
0.7867	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7339	Approved
0.7733	Intermediate Similarity	NPD6942	Approved
0.7564	Intermediate Similarity	NPD7645	Phase 2
0.747	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6926	Approved
0.7368	Intermediate Similarity	NPD6924	Approved
0.7342	Intermediate Similarity	NPD6929	Approved
0.7313	Intermediate Similarity	NPD4219	Approved
0.7284	Intermediate Similarity	NPD3667	Approved
0.725	Intermediate Similarity	NPD6930	Phase 2
0.725	Intermediate Similarity	NPD6931	Approved
0.725	Intermediate Similarity	NPD7514	Phase 3
0.725	Intermediate Similarity	NPD7332	Phase 2
0.725	Intermediate Similarity	NPD7525	Registered
0.7215	Intermediate Similarity	NPD7145	Approved
0.72	Intermediate Similarity	NPD7144	Approved
0.72	Intermediate Similarity	NPD7143	Approved
0.7179	Intermediate Similarity	NPD6933	Approved
0.716	Intermediate Similarity	NPD6902	Approved
0.7143	Intermediate Similarity	NPD4784	Approved
0.7143	Intermediate Similarity	NPD4785	Approved
0.7108	Intermediate Similarity	NPD4786	Approved
0.7108	Intermediate Similarity	NPD3666	Approved
0.7108	Intermediate Similarity	NPD3133	Approved
0.7108	Intermediate Similarity	NPD3665	Phase 1
0.7105	Intermediate Similarity	NPD7151	Approved
0.7105	Intermediate Similarity	NPD4243	Approved
0.7105	Intermediate Similarity	NPD7152	Approved
0.7105	Intermediate Similarity	NPD7150	Approved
0.7089	Intermediate Similarity	NPD5776	Phase 2
0.7089	Intermediate Similarity	NPD6925	Approved
0.7067	Intermediate Similarity	NPD6922	Approved
0.7067	Intermediate Similarity	NPD6923	Approved
0.7037	Intermediate Similarity	NPD4748	Discontinued
0.6988	Remote Similarity	NPD6695	Phase 3
0.6941	Remote Similarity	NPD4623	Approved
0.6941	Remote Similarity	NPD3618	Phase 1
0.6941	Remote Similarity	NPD5279	Phase 3
0.6941	Remote Similarity	NPD4519	Discontinued
0.6914	Remote Similarity	NPD4195	Approved
0.6905	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6932	Approved
0.6835	Remote Similarity	NPD5275	Approved
0.6835	Remote Similarity	NPD4190	Phase 3
0.6829	Remote Similarity	NPD7509	Discontinued
0.6824	Remote Similarity	NPD6893	Approved
0.6795	Remote Similarity	NPD4732	Discontinued
0.679	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6898	Phase 1
0.6742	Remote Similarity	NPD6079	Approved
0.6705	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6556	Remote Similarity	NPD7515	Phase 2
0.6556	Remote Similarity	NPD6411	Approved
0.6552	Remote Similarity	NPD5690	Phase 2
0.6517	Remote Similarity	NPD4753	Phase 2
0.6512	Remote Similarity	NPD3668	Phase 3
0.6506	Remote Similarity	NPD6683	Phase 2
0.6484	Remote Similarity	NPD4202	Approved
0.6471	Remote Similarity	NPD4221	Approved
0.6471	Remote Similarity	NPD4223	Phase 3
0.6458	Remote Similarity	NPD5211	Phase 2
0.6452	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5221	Approved
0.6452	Remote Similarity	NPD5222	Approved
0.6437	Remote Similarity	NPD1696	Phase 3
0.6429	Remote Similarity	NPD4822	Approved
0.6429	Remote Similarity	NPD4695	Discontinued
0.6429	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4821	Approved
0.6429	Remote Similarity	NPD4820	Approved
0.6429	Remote Similarity	NPD4819	Approved
0.6421	Remote Similarity	NPD7640	Approved
0.6421	Remote Similarity	NPD7639	Approved
0.6395	Remote Similarity	NPD5362	Discontinued
0.6395	Remote Similarity	NPD5331	Approved
0.6395	Remote Similarity	NPD5332	Approved
0.6386	Remote Similarity	NPD4271	Approved
0.6386	Remote Similarity	NPD4268	Approved
0.6383	Remote Similarity	NPD5173	Approved
0.6374	Remote Similarity	NPD7087	Discontinued
0.6374	Remote Similarity	NPD7637	Suspended
0.6364	Remote Similarity	NPD5280	Approved
0.6364	Remote Similarity	NPD4694	Approved
0.6353	Remote Similarity	NPD4790	Discontinued
0.6351	Remote Similarity	NPD4194	Approved
0.6351	Remote Similarity	NPD4193	Approved
0.6351	Remote Similarity	NPD4192	Approved
0.6351	Remote Similarity	NPD4191	Approved
0.6344	Remote Similarity	NPD4629	Approved
0.6344	Remote Similarity	NPD5210	Approved
0.6333	Remote Similarity	NPD6101	Approved
0.6333	Remote Similarity	NPD6051	Approved
0.6333	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5141	Approved
0.6322	Remote Similarity	NPD4197	Approved
0.6322	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5290	Discontinued
0.6316	Remote Similarity	NPD4225	Approved
0.6316	Remote Similarity	NPD7638	Approved
0.6308	Remote Similarity	NPD4265	Approved
0.6304	Remote Similarity	NPD6399	Phase 3
0.6279	Remote Similarity	NPD4269	Approved
0.6279	Remote Similarity	NPD4270	Approved
0.6277	Remote Similarity	NPD4697	Phase 3
0.6264	Remote Similarity	NPD7136	Phase 2
0.625	Remote Similarity	NPD5286	Approved
0.625	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD1694	Approved
0.625	Remote Similarity	NPD5329	Approved
0.625	Remote Similarity	NPD4696	Approved
0.6237	Remote Similarity	NPD7748	Approved
0.6235	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4755	Approved
0.6207	Remote Similarity	NPD7154	Phase 3
0.6196	Remote Similarity	NPD5281	Approved
0.6196	Remote Similarity	NPD5284	Approved
0.619	Remote Similarity	NPD3617	Approved
0.6186	Remote Similarity	NPD5223	Approved
0.618	Remote Similarity	NPD5330	Approved
0.618	Remote Similarity	NPD7334	Approved
0.618	Remote Similarity	NPD4690	Approved
0.618	Remote Similarity	NPD4693	Phase 3
0.618	Remote Similarity	NPD4688	Approved
0.618	Remote Similarity	NPD7146	Approved
0.618	Remote Similarity	NPD6409	Approved
0.618	Remote Similarity	NPD5205	Approved
0.618	Remote Similarity	NPD6684	Approved
0.618	Remote Similarity	NPD4689	Approved
0.618	Remote Similarity	NPD7521	Approved
0.618	Remote Similarity	NPD4138	Approved
0.617	Remote Similarity	NPD5695	Phase 3
0.6163	Remote Similarity	NPD4139	Approved
0.6163	Remote Similarity	NPD4692	Approved
0.6145	Remote Similarity	NPD1346	Approved
0.6122	Remote Similarity	NPD5224	Approved
0.6122	Remote Similarity	NPD4633	Approved
0.6122	Remote Similarity	NPD5226	Approved
0.6122	Remote Similarity	NPD5225	Approved
0.6092	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5785	Approved
0.6082	Remote Similarity	NPD4700	Approved
0.6067	Remote Similarity	NPD5363	Approved
0.6067	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5174	Approved
0.6061	Remote Similarity	NPD5175	Approved
0.6047	Remote Similarity	NPD4252	Approved
0.6044	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD4722	Approved
0.6044	Remote Similarity	NPD4723	Approved
0.6044	Remote Similarity	NPD4518	Approved
0.6044	Remote Similarity	NPD6903	Approved
0.6042	Remote Similarity	NPD6084	Phase 2
0.6042	Remote Similarity	NPD6083	Phase 2
0.6042	Remote Similarity	NPD7902	Approved
0.6026	Remote Similarity	NPD7331	Phase 2
0.6024	Remote Similarity	NPD8039	Approved
0.6023	Remote Similarity	NPD4788	Approved
0.6	Remote Similarity	NPD5786	Approved
0.6	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6	Remote Similarity	NPD15	Approved
0.6	Remote Similarity	NPD791	Approved
0.6	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.597	Remote Similarity	NPD385	Approved
0.597	Remote Similarity	NPD384	Approved
0.5918	Remote Similarity	NPD6404	Discontinued
0.5914	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD4096	Approved
0.5904	Remote Similarity	NPD4687	Approved
0.59	Remote Similarity	NPD4754	Approved
0.59	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD7341	Phase 2
0.5897	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5697	Approved
0.587	Remote Similarity	NPD5737	Approved
0.587	Remote Similarity	NPD6672	Approved
0.5862	Remote Similarity	NPD5368	Approved
0.5859	Remote Similarity	NPD4159	Approved
0.5843	Remote Similarity	NPD6110	Phase 1
0.5833	Remote Similarity	NPD7115	Discovery
0.5825	Remote Similarity	NPD6011	Approved
0.5825	Remote Similarity	NPD6899	Approved
0.5825	Remote Similarity	NPD4730	Approved
0.5825	Remote Similarity	NPD4729	Approved
0.5825	Remote Similarity	NPD5168	Approved
0.5825	Remote Similarity	NPD6881	Approved
0.5824	Remote Similarity	NPD4249	Approved
0.5816	Remote Similarity	NPD5696	Approved
0.5802	Remote Similarity	NPD4137	Phase 3

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