NPASS Compound

Structure

CID325003 OpenBabel06191716182D 23 24 0 0 1 0 0 0 0 0999 V2000 -4.4152 -7.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0850 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -6.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 14 1 0 0 0 0 3 14 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 2 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 15 1 0 0 0 0 12 15 1 0 0 0 0 12 18 2 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 15 20 2 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	350.552
LogP:	6.141
LogD:	4.573
LogS:	-4.193
# 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:	0.564
Synthetic Accessibility Score:	3.73
Fsp3:	0.5
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:	-4.754
MDCK Permeability:	2.56928033195436e-05
Pgp-inhibitor:	0.052
Pgp-substrate:	0.662
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.794
30% Bioavailability (F30%):	0.836

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.151
Plasma Protein Binding (PPB):	98.8564224243164%
Volume Distribution (VD):	4.265
Pgp-substrate:	2.9384233951568604%

ADMET: Metabolism

CYP1A2-inhibitor:	0.916
CYP1A2-substrate:	0.5
CYP2C19-inhibitor:	0.699
CYP2C19-substrate:	0.339
CYP2C9-inhibitor:	0.385
CYP2C9-substrate:	0.97
CYP2D6-inhibitor:	0.669
CYP2D6-substrate:	0.758
CYP3A4-inhibitor:	0.404
CYP3A4-substrate:	0.176

ADMET: Excretion

Clearance (CL):	14.78
Half-life (T1/2):	0.214

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.58
Drug-inuced Liver Injury (DILI):	0.198
AMES Toxicity:	0.232
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.87
Skin Sensitization:	0.902
Carcinogencity:	0.386
Eye Corrosion:	0.003
Eye Irritation:	0.231
Respiratory Toxicity:	0.896

Download Data

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

Natural Product: NPC325003

Natural Product ID:	NPC325003
*Common Name:**	(E)-4-(Hept-1-Enyl)-7-(3-Methylbut-2-Enyl)-2,3-Dihydrobenzofuran-2,5-Diol
IUPAC Name:	4-[(E)-hept-1-enyl]-7-(3-methylbut-2-enyl)-2,3-dihydro-1-benzofuran-2,5-diol
Synonyms:
Standard InCHIKey:	GWSQXMVDKLYNRT-CMDGGOBGSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-4-5-6-7-8-9-16-17-13-19(22)23-20(17)15(12-18(16)21)11-10-14(2)3/h8-10,12,19,21-22H,4-7,11,13H2,1-3H3/b9-8+
SMILES:	CCCCCC=CC1=C(C=C(C2=C1CC(O2)O)CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813663
PubChem CID:	53388785
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004189] Coumarans

*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
NPO30824	Eurotium repens	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667972]

☑ 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
Others	3

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	Activity	<	40.0	%	PMID[529889]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	Activity	=	51.4	%	PMID[529889]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Activity	<	40.0	%	PMID[529889]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	IC50	=	32400.0	nM	PMID[529889]

☑ 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 NPC325003 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	343
0.1-0.2	1609
0.2-0.3	4118
0.3-0.4	12437
0.4-0.5	6386
0.5-0.6	5585
0.6-0.7	9733
0.7-0.8	2388
0.8-0.85	87
0.85-0.9	10
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.888	High Similarity	NPC96423
0.8779	High Similarity	NPC11089
0.8667	High Similarity	NPC475628
0.8636	High Similarity	NPC196193
0.8583	High Similarity	NPC45663
0.8561	High Similarity	NPC97326
0.855	High Similarity	NPC469386
0.8516	High Similarity	NPC48623
0.8516	High Similarity	NPC168707
0.8462	Intermediate Similarity	NPC61685
0.8438	Intermediate Similarity	NPC129176
0.8438	Intermediate Similarity	NPC475529
0.8425	Intermediate Similarity	NPC38181
0.8425	Intermediate Similarity	NPC32152
0.8425	Intermediate Similarity	NPC20230
0.8406	Intermediate Similarity	NPC183781
0.8397	Intermediate Similarity	NPC252962
0.8397	Intermediate Similarity	NPC81641
0.837	Intermediate Similarity	NPC51262
0.8359	Intermediate Similarity	NPC232295
0.8359	Intermediate Similarity	NPC474131
0.8346	Intermediate Similarity	NPC139047
0.8345	Intermediate Similarity	NPC472794
0.8345	Intermediate Similarity	NPC473049
0.8308	Intermediate Similarity	NPC150026
0.8286	Intermediate Similarity	NPC472791
0.8286	Intermediate Similarity	NPC471414
0.8286	Intermediate Similarity	NPC472792
0.8281	Intermediate Similarity	NPC471449
0.8258	Intermediate Similarity	NPC476254
0.8258	Intermediate Similarity	NPC470726
0.8258	Intermediate Similarity	NPC131397
0.8254	Intermediate Similarity	NPC473718
0.8227	Intermediate Similarity	NPC253878
0.8209	Intermediate Similarity	NPC223912
0.8209	Intermediate Similarity	NPC40377
0.8201	Intermediate Similarity	NPC134260
0.8195	Intermediate Similarity	NPC470724
0.8194	Intermediate Similarity	NPC116019
0.8189	Intermediate Similarity	NPC69539
0.8168	Intermediate Similarity	NPC204535
0.8168	Intermediate Similarity	NPC46586
0.8163	Intermediate Similarity	NPC474442
0.816	Intermediate Similarity	NPC302371
0.816	Intermediate Similarity	NPC98372
0.8156	Intermediate Similarity	NPC5155
0.8154	Intermediate Similarity	NPC473875
0.8154	Intermediate Similarity	NPC100108
0.8154	Intermediate Similarity	NPC212559
0.8154	Intermediate Similarity	NPC277798
0.8148	Intermediate Similarity	NPC266868
0.8148	Intermediate Similarity	NPC25729
0.8148	Intermediate Similarity	NPC474494
0.8148	Intermediate Similarity	NPC472795
0.8148	Intermediate Similarity	NPC472796
0.8148	Intermediate Similarity	NPC472797
0.8148	Intermediate Similarity	NPC16577
0.814	Intermediate Similarity	NPC51341
0.8129	Intermediate Similarity	NPC126101
0.8129	Intermediate Similarity	NPC327735
0.8125	Intermediate Similarity	NPC187993
0.8125	Intermediate Similarity	NPC238176
0.812	Intermediate Similarity	NPC105031
0.812	Intermediate Similarity	NPC293801
0.8116	Intermediate Similarity	NPC71372
0.8112	Intermediate Similarity	NPC164183
0.811	Intermediate Similarity	NPC283169
0.8106	Intermediate Similarity	NPC474130
0.8106	Intermediate Similarity	NPC261992
0.8092	Intermediate Similarity	NPC212965
0.8088	Intermediate Similarity	NPC470727
0.808	Intermediate Similarity	NPC275627
0.8074	Intermediate Similarity	NPC81261
0.8074	Intermediate Similarity	NPC211179
0.8074	Intermediate Similarity	NPC38604
0.8069	Intermediate Similarity	NPC114505
0.8069	Intermediate Similarity	NPC224674
0.8069	Intermediate Similarity	NPC31325
0.8069	Intermediate Similarity	NPC275284
0.8069	Intermediate Similarity	NPC15956
0.8069	Intermediate Similarity	NPC213074
0.8069	Intermediate Similarity	NPC193473
0.8062	Intermediate Similarity	NPC283616
0.806	Intermediate Similarity	NPC321822
0.806	Intermediate Similarity	NPC325294
0.8058	Intermediate Similarity	NPC79957
0.8056	Intermediate Similarity	NPC476301
0.8056	Intermediate Similarity	NPC221318
0.8056	Intermediate Similarity	NPC43508
0.8049	Intermediate Similarity	NPC233320
0.8047	Intermediate Similarity	NPC242580
0.8047	Intermediate Similarity	NPC236070
0.8047	Intermediate Similarity	NPC126759
0.8045	Intermediate Similarity	NPC248557
0.8043	Intermediate Similarity	NPC177712
0.8043	Intermediate Similarity	NPC24913
0.8043	Intermediate Similarity	NPC211352
0.8043	Intermediate Similarity	NPC26394
0.8041	Intermediate Similarity	NPC476452
0.803	Intermediate Similarity	NPC77789
0.803	Intermediate Similarity	NPC120638
0.803	Intermediate Similarity	NPC18128
0.803	Intermediate Similarity	NPC188997
0.8029	Intermediate Similarity	NPC153019
0.8029	Intermediate Similarity	NPC160623
0.8028	Intermediate Similarity	NPC210192
0.8016	Intermediate Similarity	NPC474920
0.8015	Intermediate Similarity	NPC218753
0.8	Intermediate Similarity	NPC186889
0.8	Intermediate Similarity	NPC29799
0.8	Intermediate Similarity	NPC209985
0.8	Intermediate Similarity	NPC54743
0.8	Intermediate Similarity	NPC177160
0.8	Intermediate Similarity	NPC10737
0.8	Intermediate Similarity	NPC263367
0.8	Intermediate Similarity	NPC477939
0.8	Intermediate Similarity	NPC156502
0.7986	Intermediate Similarity	NPC49603
0.7986	Intermediate Similarity	NPC79429
0.7986	Intermediate Similarity	NPC471667
0.7986	Intermediate Similarity	NPC217635
0.7986	Intermediate Similarity	NPC193026
0.7986	Intermediate Similarity	NPC187616
0.7986	Intermediate Similarity	NPC211164
0.7985	Intermediate Similarity	NPC124030
0.7985	Intermediate Similarity	NPC470510
0.7971	Intermediate Similarity	NPC472798
0.7971	Intermediate Similarity	NPC289624
0.7971	Intermediate Similarity	NPC85595
0.7971	Intermediate Similarity	NPC321086
0.7971	Intermediate Similarity	NPC18842
0.7971	Intermediate Similarity	NPC230219
0.7971	Intermediate Similarity	NPC27578
0.7956	Intermediate Similarity	NPC262606
0.7941	Intermediate Similarity	NPC176590
0.7937	Intermediate Similarity	NPC469912
0.7931	Intermediate Similarity	NPC180953
0.7929	Intermediate Similarity	NPC137580
0.7926	Intermediate Similarity	NPC100414
0.7926	Intermediate Similarity	NPC43000
0.7923	Intermediate Similarity	NPC329980
0.7923	Intermediate Similarity	NPC63010
0.7917	Intermediate Similarity	NPC258083
0.7917	Intermediate Similarity	NPC477616
0.791	Intermediate Similarity	NPC147896
0.791	Intermediate Similarity	NPC276962
0.791	Intermediate Similarity	NPC190086
0.7907	Intermediate Similarity	NPC154256
0.7907	Intermediate Similarity	NPC290470
0.7905	Intermediate Similarity	NPC98624
0.7905	Intermediate Similarity	NPC183380
0.7902	Intermediate Similarity	NPC265075
0.7899	Intermediate Similarity	NPC129784
0.7899	Intermediate Similarity	NPC129106
0.7899	Intermediate Similarity	NPC150011
0.7899	Intermediate Similarity	NPC300875
0.7899	Intermediate Similarity	NPC268917
0.7899	Intermediate Similarity	NPC472590
0.7899	Intermediate Similarity	NPC12875
0.7899	Intermediate Similarity	NPC196765
0.7899	Intermediate Similarity	NPC228369
0.7899	Intermediate Similarity	NPC206224
0.7899	Intermediate Similarity	NPC476166
0.7899	Intermediate Similarity	NPC164574
0.7899	Intermediate Similarity	NPC118114
0.7899	Intermediate Similarity	NPC280653
0.7899	Intermediate Similarity	NPC207892
0.7899	Intermediate Similarity	NPC17343
0.7899	Intermediate Similarity	NPC236014
0.7895	Intermediate Similarity	NPC152946
0.7895	Intermediate Similarity	NPC302211
0.7895	Intermediate Similarity	NPC74137
0.7895	Intermediate Similarity	NPC57199
0.7891	Intermediate Similarity	NPC161696
0.7891	Intermediate Similarity	NPC470837
0.7891	Intermediate Similarity	NPC159697
0.7891	Intermediate Similarity	NPC130959
0.7891	Intermediate Similarity	NPC474795
0.7891	Intermediate Similarity	NPC71726
0.7891	Intermediate Similarity	NPC303013
0.7891	Intermediate Similarity	NPC474940
0.7883	Intermediate Similarity	NPC222108
0.7883	Intermediate Similarity	NPC96719
0.7877	Intermediate Similarity	NPC33832
0.7874	Intermediate Similarity	NPC228452
0.7872	Intermediate Similarity	NPC104167
0.7872	Intermediate Similarity	NPC476698
0.7872	Intermediate Similarity	NPC472800
0.7868	Intermediate Similarity	NPC108164
0.7868	Intermediate Similarity	NPC473221
0.7867	Intermediate Similarity	NPC469699
0.7863	Intermediate Similarity	NPC85895
0.7863	Intermediate Similarity	NPC137294
0.7863	Intermediate Similarity	NPC184302
0.7862	Intermediate Similarity	NPC133251
0.7857	Intermediate Similarity	NPC473107
0.7857	Intermediate Similarity	NPC132720
0.7857	Intermediate Similarity	NPC16485
0.7857	Intermediate Similarity	NPC170779
0.7857	Intermediate Similarity	NPC90083

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 NPC325003 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	954
0.2-0.3	1792
0.3-0.4	2784
0.4-0.5	1646
0.5-0.6	1052
0.6-0.7	528
0.7-0.8	77
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8898	High Similarity	NPD6696	Suspended
0.8148	Intermediate Similarity	NPD4625	Phase 3
0.8134	Intermediate Similarity	NPD2861	Phase 2
0.811	Intermediate Similarity	NPD6671	Approved
0.8095	Intermediate Similarity	NPD1398	Phase 1
0.8047	Intermediate Similarity	NPD7340	Approved
0.7956	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD4626	Approved
0.7863	Intermediate Similarity	NPD5691	Approved
0.7836	Intermediate Similarity	NPD4749	Approved
0.7826	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1611	Approved
0.782	Intermediate Similarity	NPD1091	Approved
0.782	Intermediate Similarity	NPD3705	Approved
0.7794	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6674	Discontinued
0.7744	Intermediate Similarity	NPD3496	Discontinued
0.7714	Intermediate Similarity	NPD4060	Phase 1
0.7669	Intermediate Similarity	NPD1778	Approved
0.7639	Intermediate Similarity	NPD5762	Approved
0.7639	Intermediate Similarity	NPD5763	Approved
0.7597	Intermediate Similarity	NPD7635	Approved
0.7574	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD968	Approved
0.7517	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6004	Phase 3
0.7517	Intermediate Similarity	NPD6005	Phase 3
0.7517	Intermediate Similarity	NPD6002	Phase 3
0.7483	Intermediate Similarity	NPD2157	Approved
0.7482	Intermediate Similarity	NPD1712	Approved
0.7465	Intermediate Similarity	NPD4140	Approved
0.7444	Intermediate Similarity	NPD7644	Approved
0.7429	Intermediate Similarity	NPD4908	Phase 1
0.7426	Intermediate Similarity	NPD1610	Phase 2
0.7422	Intermediate Similarity	NPD2684	Approved
0.7413	Intermediate Similarity	NPD5735	Approved
0.7407	Intermediate Similarity	NPD5125	Phase 3
0.7407	Intermediate Similarity	NPD5126	Approved
0.7391	Intermediate Similarity	NPD8651	Approved
0.7357	Intermediate Similarity	NPD2237	Approved
0.7351	Intermediate Similarity	NPD6090	Discontinued
0.7344	Intermediate Similarity	NPD290	Approved
0.7333	Intermediate Similarity	NPD1357	Approved
0.7328	Intermediate Similarity	NPD1138	Approved
0.7324	Intermediate Similarity	NPD7985	Registered
0.7319	Intermediate Similarity	NPD5327	Phase 3
0.7293	Intermediate Similarity	NPD7157	Approved
0.7293	Intermediate Similarity	NPD709	Approved
0.7285	Intermediate Similarity	NPD2534	Approved
0.7285	Intermediate Similarity	NPD2532	Approved
0.7285	Intermediate Similarity	NPD2533	Approved
0.728	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD1548	Phase 1
0.7252	Intermediate Similarity	NPD1139	Approved
0.7252	Intermediate Similarity	NPD1137	Approved
0.7244	Intermediate Similarity	NPD5929	Approved
0.7241	Intermediate Similarity	NPD4097	Suspended
0.7237	Intermediate Similarity	NPD2675	Approved
0.7237	Intermediate Similarity	NPD2676	Approved
0.7236	Intermediate Similarity	NPD844	Approved
0.7222	Intermediate Similarity	NPD1613	Approved
0.7222	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6100	Approved
0.7211	Intermediate Similarity	NPD6099	Approved
0.7197	Intermediate Similarity	NPD7843	Approved
0.7179	Intermediate Similarity	NPD37	Approved
0.7177	Intermediate Similarity	NPD288	Approved
0.7171	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3690	Phase 2
0.7163	Intermediate Similarity	NPD3691	Phase 2
0.7152	Intermediate Similarity	NPD4966	Approved
0.7152	Intermediate Similarity	NPD4965	Approved
0.7152	Intermediate Similarity	NPD4967	Phase 2
0.7152	Intermediate Similarity	NPD5058	Phase 3
0.7143	Intermediate Similarity	NPD4108	Discontinued
0.7143	Intermediate Similarity	NPD1283	Approved
0.7143	Intermediate Similarity	NPD1653	Approved
0.7133	Intermediate Similarity	NPD3027	Phase 3
0.7133	Intermediate Similarity	NPD3892	Phase 2
0.7133	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6353	Approved
0.7122	Intermediate Similarity	NPD2233	Approved
0.7122	Intermediate Similarity	NPD2231	Phase 2
0.7122	Intermediate Similarity	NPD1608	Approved
0.7122	Intermediate Similarity	NPD2232	Approved
0.7122	Intermediate Similarity	NPD2230	Approved
0.7122	Intermediate Similarity	NPD2235	Phase 2
0.7114	Intermediate Similarity	NPD7037	Approved
0.7108	Intermediate Similarity	NPD6559	Discontinued
0.7103	Intermediate Similarity	NPD2238	Phase 2
0.7103	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3620	Phase 2
0.7099	Intermediate Similarity	NPD4750	Phase 3
0.7097	Intermediate Similarity	NPD3226	Approved
0.7086	Intermediate Similarity	NPD2677	Approved
0.708	Intermediate Similarity	NPD3445	Approved
0.708	Intermediate Similarity	NPD3444	Approved
0.708	Intermediate Similarity	NPD1651	Approved
0.708	Intermediate Similarity	NPD3443	Approved
0.7077	Intermediate Similarity	NPD2342	Discontinued
0.7071	Intermediate Similarity	NPD3685	Discontinued
0.7063	Intermediate Similarity	NPD6234	Discontinued
0.7063	Intermediate Similarity	NPD5709	Phase 3
0.7063	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD422	Phase 1
0.705	Intermediate Similarity	NPD776	Approved
0.7047	Intermediate Similarity	NPD2346	Discontinued
0.7047	Intermediate Similarity	NPD1375	Discontinued
0.7042	Intermediate Similarity	NPD6584	Phase 3
0.7042	Intermediate Similarity	NPD4624	Approved
0.7039	Intermediate Similarity	NPD6666	Approved
0.7039	Intermediate Similarity	NPD6667	Approved
0.703	Intermediate Similarity	NPD5844	Phase 1
0.7027	Intermediate Similarity	NPD7033	Discontinued
0.7024	Intermediate Similarity	NPD8313	Approved
0.7024	Intermediate Similarity	NPD8312	Approved
0.702	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4666	Phase 3
0.7013	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3091	Approved
0.7007	Intermediate Similarity	NPD6653	Approved
0.7	Intermediate Similarity	NPD1840	Phase 2
0.6993	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD228	Approved
0.6987	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2979	Phase 3
0.698	Remote Similarity	NPD4477	Approved
0.698	Remote Similarity	NPD4476	Approved
0.698	Remote Similarity	NPD2935	Discontinued
0.6975	Remote Similarity	NPD7199	Phase 2
0.697	Remote Similarity	NPD7228	Approved
0.6957	Remote Similarity	NPD5585	Approved
0.6944	Remote Similarity	NPD600	Approved
0.6944	Remote Similarity	NPD596	Approved
0.694	Remote Similarity	NPD821	Approved
0.6939	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5124	Phase 1
0.6935	Remote Similarity	NPD845	Approved
0.6929	Remote Similarity	NPD3092	Approved
0.6929	Remote Similarity	NPD1281	Approved
0.6923	Remote Similarity	NPD558	Phase 2
0.6918	Remote Similarity	NPD8455	Phase 2
0.6913	Remote Similarity	NPD5588	Approved
0.6912	Remote Similarity	NPD6387	Discontinued
0.6908	Remote Similarity	NPD4628	Phase 3
0.6906	Remote Similarity	NPD17	Approved
0.6875	Remote Similarity	NPD2563	Approved
0.6875	Remote Similarity	NPD2560	Approved
0.6853	Remote Similarity	NPD2797	Approved
0.6853	Remote Similarity	NPD3094	Phase 2
0.6849	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4536	Approved
0.6846	Remote Similarity	NPD4538	Approved
0.6842	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD497	Approved
0.6831	Remote Similarity	NPD6582	Phase 2
0.6831	Remote Similarity	NPD1669	Approved
0.6831	Remote Similarity	NPD6583	Phase 3
0.6829	Remote Similarity	NPD7229	Phase 3
0.6824	Remote Similarity	NPD6355	Discontinued
0.6821	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7819	Suspended
0.6803	Remote Similarity	NPD839	Approved
0.6803	Remote Similarity	NPD840	Approved
0.6803	Remote Similarity	NPD8032	Phase 2
0.68	Remote Similarity	NPD2155	Approved
0.68	Remote Similarity	NPD2156	Approved
0.68	Remote Similarity	NPD2154	Approved
0.6795	Remote Similarity	NPD6273	Approved
0.6788	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2970	Approved
0.6788	Remote Similarity	NPD2969	Approved
0.6788	Remote Similarity	NPD2557	Approved
0.6776	Remote Similarity	NPD2424	Discontinued
0.6774	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6959	Discontinued
0.6766	Remote Similarity	NPD3818	Discontinued
0.6765	Remote Similarity	NPD496	Approved
0.6765	Remote Similarity	NPD495	Approved
0.6765	Remote Similarity	NPD592	Approved
0.6765	Remote Similarity	NPD498	Approved
0.6765	Remote Similarity	NPD5283	Phase 1
0.6765	Remote Similarity	NPD594	Approved
0.6763	Remote Similarity	NPD1182	Approved
0.6759	Remote Similarity	NPD5736	Approved
0.6755	Remote Similarity	NPD6032	Approved
0.6753	Remote Similarity	NPD3692	Discontinued
0.6748	Remote Similarity	NPD9295	Approved
0.6747	Remote Similarity	NPD27	Approved
0.6747	Remote Similarity	NPD2489	Approved
0.6736	Remote Similarity	NPD6362	Approved
0.6733	Remote Similarity	NPD7097	Phase 1
0.6731	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7446	Clinical (unspecified phase)

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