NPASS Compound

Structure

NPC18842 OpenBabel07101719402D 25 27 0 0 1 0 0 0 0 0999 V2000 2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -1.6750 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 -1.8090 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 -2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 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 -1.5878 -0.8090 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 0.0000 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0878 0.0570 0.0000 C 0 0 1 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 -0.5878 -0.8090 0.0000 C 0 0 2 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 2.6831 -4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -2.7770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 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 24 1 0 0 0 0 2 3 1 0 0 0 0 2 6 1 0 0 0 0 3 11 1 0 0 0 0 4 5 1 0 0 0 0 4 12 1 0 0 0 0 5 15 1 0 0 0 0 6 20 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 11 1 0 0 0 0 8 17 2 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 21 1 0 0 0 0 13 14 1 0 0 0 0 13 19 2 0 0 0 0 14 10 1 6 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 1 0 0 0 16 23 1 1 0 0 0 17 19 1 0 0 0 0 17 24 1 0 0 0 0 18 12 1 1 0 0 0 18 25 1 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.17
Volume:	353.706
LogP:	0.644
LogD:	0.628
LogS:	-2.505
# Rotatable Bonds:	6
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.569
Synthetic Accessibility Score:	4.169
Fsp3:	0.579
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:	-5.031
MDCK Permeability:	2.1230796846793965e-05
Pgp-inhibitor:	0.053
Pgp-substrate:	0.756
Human Intestinal Absorption (HIA):	0.104
20% Bioavailability (F20%):	0.113
30% Bioavailability (F30%):	0.053

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.322
Plasma Protein Binding (PPB):	47.58892059326172%
Volume Distribution (VD):	1.816
Pgp-substrate:	22.88001251220703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.424
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.63
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.327
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.329

ADMET: Excretion

Clearance (CL):	6.211
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.073
Drug-inuced Liver Injury (DILI):	0.113
AMES Toxicity:	0.165
Rat Oral Acute Toxicity:	0.412
Maximum Recommended Daily Dose:	0.826
Skin Sensitization:	0.35
Carcinogencity:	0.698
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.837

Download Data

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

Natural Product: NPC18842

Natural Product ID:	NPC18842
*Common Name:**	Difengpiol A
IUPAC Name:	(1R,2S)-4-[(2S,3R)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]cyclohex-3-ene-1,2-diol
Synonyms:
Standard InCHIKey:	RAROOKDBJRIINZ-UIBIWLFHSA-N
Standard InCHI:	InChI=1S/C19H26O6/c1-24-17-8-11(3-2-6-20)7-13-14(10-21)18(25-19(13)17)12-4-5-15(22)16(23)9-12/h7-9,14-16,18,20-23H,2-6,10H2,1H3/t14-,15+,16-,18+/m0/s1
SMILES:	OCCCc1cc2[C@H](CO)[C@H](Oc2c(c1)OC)C1=C[C@@H]([C@@H](CC1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1096427
PubChem CID:	46834275
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
NPO11871	Illicium difengpi	Species	Schisandraceae	Eukaryota	stem bark	n.a.	n.a.	PMID[20411974]
NPO11871	Illicium difengpi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11871	Illicium difengpi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11871	Illicium difengpi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11871	Illicium difengpi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[560085]

☑ 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 NPC18842 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	389
0.1-0.2	1364
0.2-0.3	3890
0.3-0.4	9601
0.4-0.5	9190
0.5-0.6	4122
0.6-0.7	9145
0.7-0.8	3863
0.8-0.85	862
0.85-0.9	247
0.9-0.95	22
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9609	High Similarity	NPC26394
0.9538	High Similarity	NPC177160
0.9538	High Similarity	NPC263367
0.9538	High Similarity	NPC10737
0.9538	High Similarity	NPC54743
0.9538	High Similarity	NPC209985
0.9538	High Similarity	NPC477939
0.9538	High Similarity	NPC29799
0.9538	High Similarity	NPC156502
0.9535	High Similarity	NPC16485
0.9531	High Similarity	NPC230219
0.9385	High Similarity	NPC187616
0.9385	High Similarity	NPC193026
0.9385	High Similarity	NPC49603
0.9318	High Similarity	NPC477938
0.9254	High Similarity	NPC263261
0.9254	High Similarity	NPC87725
0.9254	High Similarity	NPC471414
0.9219	High Similarity	NPC470084
0.9185	High Similarity	NPC253878
0.9141	High Similarity	NPC98745
0.9077	High Similarity	NPC241522
0.9077	High Similarity	NPC42300
0.9077	High Similarity	NPC92164
0.9077	High Similarity	NPC257582
0.9077	High Similarity	NPC64201
0.9077	High Similarity	NPC187998
0.9077	High Similarity	NPC77040
0.9077	High Similarity	NPC174495
0.9077	High Similarity	NPC242807
0.9077	High Similarity	NPC145305
0.9077	High Similarity	NPC153739
0.9062	High Similarity	NPC206882
0.9051	High Similarity	NPC264706
0.9051	High Similarity	NPC284881
0.9051	High Similarity	NPC474444
0.9051	High Similarity	NPC93433
0.9044	High Similarity	NPC131971
0.9008	High Similarity	NPC277804
0.9	High Similarity	NPC475875
0.8986	High Similarity	NPC43508
0.8986	High Similarity	NPC181615
0.8986	High Similarity	NPC163898
0.8986	High Similarity	NPC476301
0.8978	High Similarity	NPC102044
0.8978	High Similarity	NPC47633
0.8978	High Similarity	NPC85264
0.8971	High Similarity	NPC311530
0.8947	High Similarity	NPC478085
0.8931	High Similarity	NPC143483
0.8923	High Similarity	NPC11258
0.8923	High Similarity	NPC45774
0.8923	High Similarity	NPC129570
0.8923	High Similarity	NPC184733
0.8923	High Similarity	NPC21867
0.8923	High Similarity	NPC128208
0.8923	High Similarity	NPC282703
0.8923	High Similarity	NPC472968
0.8921	High Similarity	NPC260397
0.8913	High Similarity	NPC280092
0.8913	High Similarity	NPC63879
0.8913	High Similarity	NPC471667
0.8913	High Similarity	NPC217635
0.8913	High Similarity	NPC45257
0.8913	High Similarity	NPC12641
0.8913	High Similarity	NPC79429
0.8913	High Similarity	NPC93323
0.8906	High Similarity	NPC94276
0.8906	High Similarity	NPC109822
0.8897	High Similarity	NPC184797
0.8897	High Similarity	NPC254759
0.8897	High Similarity	NPC309124
0.8897	High Similarity	NPC160283
0.8881	High Similarity	NPC93783
0.8881	High Similarity	NPC174191
0.8864	High Similarity	NPC40432
0.8864	High Similarity	NPC158079
0.8864	High Similarity	NPC7171
0.8864	High Similarity	NPC27843
0.8864	High Similarity	NPC115207
0.8864	High Similarity	NPC161557
0.8864	High Similarity	NPC228346
0.8857	High Similarity	NPC31325
0.8857	High Similarity	NPC114505
0.8857	High Similarity	NPC275284
0.8857	High Similarity	NPC101376
0.8857	High Similarity	NPC213074
0.8857	High Similarity	NPC15956
0.8857	High Similarity	NPC193473
0.8857	High Similarity	NPC224674
0.8846	High Similarity	NPC163332
0.8846	High Similarity	NPC41706
0.8846	High Similarity	NPC111247
0.8846	High Similarity	NPC147821
0.8846	High Similarity	NPC165045
0.8846	High Similarity	NPC319625
0.8846	High Similarity	NPC292056
0.8846	High Similarity	NPC118533
0.8846	High Similarity	NPC183181
0.8846	High Similarity	NPC118787
0.8841	High Similarity	NPC477616
0.8837	High Similarity	NPC81641
0.8832	High Similarity	NPC247291
0.8824	High Similarity	NPC70682
0.8824	High Similarity	NPC260741
0.8824	High Similarity	NPC473739
0.8824	High Similarity	NPC236306
0.8824	High Similarity	NPC232164
0.8824	High Similarity	NPC292882
0.8815	High Similarity	NPC327735
0.8815	High Similarity	NPC77861
0.8815	High Similarity	NPC470802
0.8806	High Similarity	NPC244983
0.8806	High Similarity	NPC287745
0.8806	High Similarity	NPC326095
0.8797	High Similarity	NPC207400
0.8797	High Similarity	NPC175067
0.8797	High Similarity	NPC204215
0.8797	High Similarity	NPC181049
0.8794	High Similarity	NPC473408
0.8769	High Similarity	NPC178284
0.8769	High Similarity	NPC58607
0.8769	High Similarity	NPC191037
0.8768	High Similarity	NPC107161
0.876	High Similarity	NPC114901
0.876	High Similarity	NPC293701
0.876	High Similarity	NPC48990
0.8759	High Similarity	NPC27495
0.8759	High Similarity	NPC259519
0.875	High Similarity	NPC71090
0.8741	High Similarity	NPC256262
0.8741	High Similarity	NPC234333
0.8741	High Similarity	NPC61946
0.8741	High Similarity	NPC260898
0.8741	High Similarity	NPC47398
0.8731	High Similarity	NPC158331
0.8731	High Similarity	NPC263064
0.8731	High Similarity	NPC475840
0.873	High Similarity	NPC135961
0.8723	High Similarity	NPC21776
0.8723	High Similarity	NPC16269
0.8714	High Similarity	NPC469557
0.8714	High Similarity	NPC221318
0.8714	High Similarity	NPC180953
0.8712	High Similarity	NPC3439
0.8712	High Similarity	NPC5851
0.8712	High Similarity	NPC190629
0.8712	High Similarity	NPC86030
0.8712	High Similarity	NPC210623
0.8712	High Similarity	NPC285339
0.8712	High Similarity	NPC470258
0.8712	High Similarity	NPC273295
0.8712	High Similarity	NPC226788
0.8712	High Similarity	NPC222004
0.8712	High Similarity	NPC218856
0.8712	High Similarity	NPC202582
0.8702	High Similarity	NPC21563
0.8702	High Similarity	NPC5428
0.8696	High Similarity	NPC35216
0.8696	High Similarity	NPC471389
0.8692	High Similarity	NPC470726
0.8692	High Similarity	NPC148627
0.8692	High Similarity	NPC194519
0.8686	High Similarity	NPC471388
0.8686	High Similarity	NPC260842
0.8676	High Similarity	NPC16435
0.8676	High Similarity	NPC265433
0.8676	High Similarity	NPC306441
0.8676	High Similarity	NPC472334
0.8676	High Similarity	NPC78047
0.8676	High Similarity	NPC126101
0.8676	High Similarity	NPC162659
0.8676	High Similarity	NPC248727
0.8676	High Similarity	NPC472336
0.8676	High Similarity	NPC270456
0.8672	High Similarity	NPC126935
0.8672	High Similarity	NPC476343
0.8672	High Similarity	NPC312713
0.8672	High Similarity	NPC57268
0.8672	High Similarity	NPC172676
0.8672	High Similarity	NPC470804
0.8672	High Similarity	NPC65933
0.8672	High Similarity	NPC216929
0.8671	High Similarity	NPC472709
0.8671	High Similarity	NPC98624
0.8671	High Similarity	NPC472710
0.8667	High Similarity	NPC90083
0.8667	High Similarity	NPC170779
0.8667	High Similarity	NPC471942
0.8667	High Similarity	NPC67247
0.8662	High Similarity	NPC236166
0.8662	High Similarity	NPC270751
0.8657	High Similarity	NPC2190
0.8657	High Similarity	NPC4940
0.8652	High Similarity	NPC324492
0.8652	High Similarity	NPC317053
0.8647	High Similarity	NPC469612
0.8647	High Similarity	NPC469614
0.8647	High Similarity	NPC470727
0.8643	High Similarity	NPC473108

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 NPC18842 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	869
0.2-0.3	1967
0.3-0.4	2672
0.4-0.5	1604
0.5-0.6	942
0.6-0.7	636
0.7-0.8	144
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8433	Intermediate Similarity	NPD3027	Phase 3
0.8382	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD1613	Approved
0.8298	Intermediate Similarity	NPD6674	Discontinued
0.8195	Intermediate Similarity	NPD8651	Approved
0.8148	Intermediate Similarity	NPD2861	Phase 2
0.8148	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD3705	Approved
0.8088	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD3620	Phase 2
0.7986	Intermediate Similarity	NPD4060	Phase 1
0.7986	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD5283	Phase 1
0.7857	Intermediate Similarity	NPD2684	Approved
0.7852	Intermediate Similarity	NPD4749	Approved
0.7846	Intermediate Similarity	NPD7157	Approved
0.7836	Intermediate Similarity	NPD1091	Approved
0.7826	Intermediate Similarity	NPD4908	Phase 1
0.7812	Intermediate Similarity	NPD228	Approved
0.781	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD6696	Suspended
0.7778	Intermediate Similarity	NPD2563	Approved
0.7778	Intermediate Similarity	NPD2560	Approved
0.7778	Intermediate Similarity	NPD5763	Approved
0.7778	Intermediate Similarity	NPD5762	Approved
0.7778	Intermediate Similarity	NPD290	Approved
0.7763	Intermediate Similarity	NPD37	Approved
0.7762	Intermediate Similarity	NPD5588	Approved
0.7752	Intermediate Similarity	NPD7843	Approved
0.7744	Intermediate Similarity	NPD1357	Approved
0.7727	Intermediate Similarity	NPD4965	Approved
0.7727	Intermediate Similarity	NPD4967	Phase 2
0.7727	Intermediate Similarity	NPD4966	Approved
0.7704	Intermediate Similarity	NPD1610	Phase 2
0.7692	Intermediate Similarity	NPD4538	Approved
0.7692	Intermediate Similarity	NPD4536	Approved
0.7692	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD5735	Approved
0.7658	Intermediate Similarity	NPD2970	Approved
0.7658	Intermediate Similarity	NPD2969	Approved
0.7655	Intermediate Similarity	NPD6002	Phase 3
0.7655	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD6004	Phase 3
0.7655	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD6005	Phase 3
0.7635	Intermediate Similarity	NPD5058	Phase 3
0.7628	Intermediate Similarity	NPD6234	Discontinued
0.7619	Intermediate Similarity	NPD6331	Phase 2
0.7603	Intermediate Similarity	NPD2424	Discontinued
0.7597	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6671	Approved
0.7568	Intermediate Similarity	NPD2677	Approved
0.7552	Intermediate Similarity	NPD6355	Discontinued
0.7551	Intermediate Similarity	NPD4237	Approved
0.7551	Intermediate Similarity	NPD4236	Phase 3
0.7534	Intermediate Similarity	NPD1375	Discontinued
0.7532	Intermediate Similarity	NPD7199	Phase 2
0.7532	Intermediate Similarity	NPD1934	Approved
0.7518	Intermediate Similarity	NPD4625	Phase 3
0.7517	Intermediate Similarity	NPD5960	Phase 3
0.75	Intermediate Similarity	NPD2489	Approved
0.75	Intermediate Similarity	NPD6653	Approved
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD27	Approved
0.75	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD4110	Phase 3
0.75	Intermediate Similarity	NPD3018	Phase 2
0.7484	Intermediate Similarity	NPD3051	Approved
0.7484	Intermediate Similarity	NPD6071	Discontinued
0.7468	Intermediate Similarity	NPD5494	Approved
0.7466	Intermediate Similarity	NPD2161	Phase 2
0.7431	Intermediate Similarity	NPD5124	Phase 1
0.7431	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1548	Phase 1
0.7407	Intermediate Similarity	NPD7228	Approved
0.7389	Intermediate Similarity	NPD3882	Suspended
0.7385	Intermediate Similarity	NPD3022	Approved
0.7385	Intermediate Similarity	NPD3021	Approved
0.7381	Intermediate Similarity	NPD291	Approved
0.7379	Intermediate Similarity	NPD2157	Approved
0.7372	Intermediate Similarity	NPD5772	Approved
0.7372	Intermediate Similarity	NPD5773	Approved
0.7368	Intermediate Similarity	NPD7526	Approved
0.7368	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD52	Approved
0.7362	Intermediate Similarity	NPD5844	Phase 1
0.7361	Intermediate Similarity	NPD2238	Phase 2
0.7361	Intermediate Similarity	NPD1558	Phase 1
0.7361	Intermediate Similarity	NPD4140	Approved
0.7351	Intermediate Similarity	NPD1774	Approved
0.7349	Intermediate Similarity	NPD7312	Approved
0.7349	Intermediate Similarity	NPD7313	Approved
0.7349	Intermediate Similarity	NPD7311	Approved
0.7349	Intermediate Similarity	NPD7310	Approved
0.7338	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5327	Phase 3
0.7338	Intermediate Similarity	NPD2983	Phase 2
0.7338	Intermediate Similarity	NPD2982	Phase 2
0.7329	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5177	Phase 3
0.7312	Intermediate Similarity	NPD8127	Discontinued
0.731	Intermediate Similarity	NPD3657	Discovery
0.7305	Intermediate Similarity	NPD3690	Phase 2
0.7305	Intermediate Similarity	NPD3691	Phase 2
0.7305	Intermediate Similarity	NPD7309	Approved
0.7301	Intermediate Similarity	NPD3818	Discontinued
0.7299	Intermediate Similarity	NPD4626	Approved
0.7292	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6166	Phase 2
0.7284	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3687	Approved
0.7273	Intermediate Similarity	NPD3686	Approved
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.7266	Intermediate Similarity	NPD2981	Phase 2
0.7266	Intermediate Similarity	NPD2235	Phase 2
0.7266	Intermediate Similarity	NPD2231	Phase 2
0.7261	Intermediate Similarity	NPD2801	Approved
0.7259	Intermediate Similarity	NPD7340	Approved
0.7246	Intermediate Similarity	NPD3496	Discontinued
0.7237	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3094	Phase 2
0.7226	Intermediate Similarity	NPD5691	Approved
0.7226	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6798	Discontinued
0.7222	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4663	Approved
0.72	Intermediate Similarity	NPD3060	Approved
0.72	Intermediate Similarity	NPD4162	Approved
0.72	Intermediate Similarity	NPD1652	Phase 2
0.719	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4123	Phase 3
0.7181	Intermediate Similarity	NPD7266	Discontinued
0.7181	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5126	Approved
0.7174	Intermediate Similarity	NPD6516	Phase 2
0.7174	Intermediate Similarity	NPD5846	Approved
0.7174	Intermediate Similarity	NPD5125	Phase 3
0.7171	Intermediate Similarity	NPD6666	Approved
0.7171	Intermediate Similarity	NPD6667	Approved
0.7164	Intermediate Similarity	NPD1398	Phase 1
0.7162	Intermediate Similarity	NPD7033	Discontinued
0.7161	Intermediate Similarity	NPD4210	Discontinued
0.7153	Intermediate Similarity	NPD7095	Approved
0.7152	Intermediate Similarity	NPD4535	Phase 3
0.7152	Intermediate Similarity	NPD3892	Phase 2
0.7152	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD8455	Phase 2
0.7143	Intermediate Similarity	NPD6353	Approved
0.7143	Intermediate Similarity	NPD4578	Approved
0.7143	Intermediate Similarity	NPD4097	Suspended
0.7143	Intermediate Similarity	NPD4577	Approved
0.7134	Intermediate Similarity	NPD6072	Discontinued
0.7133	Intermediate Similarity	NPD1712	Approved
0.7126	Intermediate Similarity	NPD7240	Approved
0.7125	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD4750	Phase 3
0.7108	Intermediate Similarity	NPD7074	Phase 3
0.7107	Intermediate Similarity	NPD3817	Phase 2
0.7105	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7985	Registered
0.7103	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5976	Discontinued
0.7095	Intermediate Similarity	NPD7097	Phase 1
0.7092	Intermediate Similarity	NPD3685	Discontinued
0.7083	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5536	Phase 2
0.7078	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7906	Approved
0.7073	Intermediate Similarity	NPD4481	Phase 3
0.7071	Intermediate Similarity	NPD422	Phase 1
0.7071	Intermediate Similarity	NPD3092	Approved
0.707	Intermediate Similarity	NPD4678	Approved
0.707	Intermediate Similarity	NPD4380	Phase 2
0.707	Intermediate Similarity	NPD4675	Approved
0.7063	Intermediate Similarity	NPD6584	Phase 3
0.7063	Intermediate Similarity	NPD558	Phase 2
0.7055	Intermediate Similarity	NPD3163	Approved
0.7055	Intermediate Similarity	NPD3162	Approved
0.7055	Intermediate Similarity	NPD6233	Phase 2
0.705	Intermediate Similarity	NPD1778	Approved
0.7048	Intermediate Similarity	NPD7054	Approved
0.7044	Intermediate Similarity	NPD2978	Approved
0.7044	Intermediate Similarity	NPD2977	Approved
0.7039	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4666	Phase 3
0.7034	Intermediate Similarity	NPD3179	Approved
0.7034	Intermediate Similarity	NPD3180	Approved
0.7032	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6559	Discontinued

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