NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	372.16
Volume:	380.389
LogP:	2.137
LogD:	2.437
LogS:	-3.467
# Rotatable Bonds:	7
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.778
Synthetic Accessibility Score:	3.329
Fsp3:	0.333
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:	-4.779
MDCK Permeability:	1.5072638234414626e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.107
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.95
Plasma Protein Binding (PPB):	68.30570220947266%
Volume Distribution (VD):	0.765
Pgp-substrate:	19.300020217895508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.863
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.886
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.758
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.798
CYP3A4-inhibitor:	0.58
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	7.562
Half-life (T1/2):	0.534

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.309
Drug-inuced Liver Injury (DILI):	0.675
AMES Toxicity:	0.726
Rat Oral Acute Toxicity:	0.106
Maximum Recommended Daily Dose:	0.324
Skin Sensitization:	0.624
Carcinogencity:	0.737
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC477938

Natural Product ID:	NPC477938
*Common Name:**	(E)-3-[(2R,3S)-3-(hydroxymethyl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-ol
IUPAC Name:	(E)-3-[(2R,3S)-3-(hydroxymethyl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-ol
Synonyms:
Standard InCHIKey:	FKFHXYWDVKLRMA-CGJGEUGISA-N
Standard InCHI:	InChI=1S/C21H24O6/c1-24-18-10-14(11-19(25-2)21(18)26-3)20-16(12-23)15-9-13(5-4-8-22)6-7-17(15)27-20/h4-7,9-11,16,20,22-23H,8,12H2,1-3H3/b5-4+/t16-,20+/m1/s1
SMILES:	COC1=CC(=CC(=C1OC)OC)[C@H]2[C@@H](C3=C(O2)C=CC(=C3)/C=C/CO)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	56659552
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	stem	n.a.	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	skin-removed stems	Pingle Town, Sichuang Province, China	2008-AUG	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22690646]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	<	30	%	PMID[21469695]

☑ 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 NPC477938 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	416
0.1-0.2	1438
0.2-0.3	3875
0.3-0.4	10892
0.4-0.5	7762
0.5-0.6	3841
0.6-0.7	6706
0.7-0.8	5849
0.8-0.85	1039
0.85-0.9	680
0.9-0.95	192
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9774	High Similarity	NPC263261
0.9774	High Similarity	NPC87725
0.9692	High Similarity	NPC26394
0.9615	High Similarity	NPC230219
0.9489	High Similarity	NPC181615
0.9474	High Similarity	NPC10737
0.9474	High Similarity	NPC177160
0.9474	High Similarity	NPC54743
0.9474	High Similarity	NPC209985
0.9474	High Similarity	NPC263367
0.9474	High Similarity	NPC29799
0.9474	High Similarity	NPC477939
0.9474	High Similarity	NPC156502
0.942	High Similarity	NPC260397
0.9416	High Similarity	NPC93323
0.9416	High Similarity	NPC280092
0.9416	High Similarity	NPC45257
0.9416	High Similarity	NPC12641
0.9407	High Similarity	NPC184797
0.9407	High Similarity	NPC254759
0.9407	High Similarity	NPC160283
0.9407	High Similarity	NPC27495
0.9407	High Similarity	NPC309124
0.9348	High Similarity	NPC469557
0.9348	High Similarity	NPC180953
0.9343	High Similarity	NPC47633
0.9343	High Similarity	NPC477616
0.9343	High Similarity	NPC102044
0.9343	High Similarity	NPC85264
0.9338	High Similarity	NPC311530
0.9333	High Similarity	NPC473739
0.9333	High Similarity	NPC232164
0.9333	High Similarity	NPC70682
0.9333	High Similarity	NPC292882
0.9333	High Similarity	NPC236306
0.9333	High Similarity	NPC260741
0.9333	High Similarity	NPC471388
0.9328	High Similarity	NPC78047
0.9323	High Similarity	NPC49603
0.9323	High Similarity	NPC287745
0.9323	High Similarity	NPC193026
0.9323	High Similarity	NPC16485
0.9323	High Similarity	NPC187616
0.9318	High Similarity	NPC18842
0.9286	High Similarity	NPC473408
0.9275	High Similarity	NPC63879
0.927	High Similarity	NPC107161
0.9254	High Similarity	NPC61946
0.9254	High Similarity	NPC256262
0.9248	High Similarity	NPC263064
0.9248	High Similarity	NPC475840
0.9248	High Similarity	NPC158331
0.9237	High Similarity	NPC222004
0.9237	High Similarity	NPC3439
0.9237	High Similarity	NPC210623
0.9237	High Similarity	NPC285339
0.9237	High Similarity	NPC226788
0.9237	High Similarity	NPC190629
0.9237	High Similarity	NPC202582
0.9237	High Similarity	NPC218856
0.9237	High Similarity	NPC470258
0.9237	High Similarity	NPC273295
0.9231	High Similarity	NPC98745
0.9231	High Similarity	NPC242032
0.9214	High Similarity	NPC101376
0.9214	High Similarity	NPC21776
0.9214	High Similarity	NPC16269
0.9209	High Similarity	NPC221318
0.9197	High Similarity	NPC471389
0.9197	High Similarity	NPC35216
0.9197	High Similarity	NPC471414
0.9197	High Similarity	NPC247291
0.9185	High Similarity	NPC265433
0.9185	High Similarity	NPC472336
0.9185	High Similarity	NPC173660
0.9185	High Similarity	NPC248727
0.9185	High Similarity	NPC16435
0.9185	High Similarity	NPC306441
0.9185	High Similarity	NPC162659
0.9185	High Similarity	NPC470802
0.9185	High Similarity	NPC472334
0.9185	High Similarity	NPC270456
0.9179	High Similarity	NPC474478
0.9179	High Similarity	NPC326095
0.9179	High Similarity	NPC244983
0.9173	High Similarity	NPC175067
0.9173	High Similarity	NPC204215
0.916	High Similarity	NPC470084
0.9154	High Similarity	NPC285725
0.9154	High Similarity	NPC112571
0.9154	High Similarity	NPC50683
0.9154	High Similarity	NPC206882
0.9149	High Similarity	NPC270751
0.9143	High Similarity	NPC324492
0.9143	High Similarity	NPC317053
0.9137	High Similarity	NPC473108
0.913	High Similarity	NPC204347
0.913	High Similarity	NPC41782
0.913	High Similarity	NPC475891
0.913	High Similarity	NPC59841
0.913	High Similarity	NPC2613
0.913	High Similarity	NPC253878
0.9124	High Similarity	NPC259519
0.9111	High Similarity	NPC234333
0.9111	High Similarity	NPC112939
0.9111	High Similarity	NPC47398
0.9111	High Similarity	NPC474206
0.9111	High Similarity	NPC195022
0.9111	High Similarity	NPC260898
0.9111	High Similarity	NPC470356
0.9111	High Similarity	NPC94750
0.9111	High Similarity	NPC121812
0.9111	High Similarity	NPC134968
0.9111	High Similarity	NPC472337
0.9111	High Similarity	NPC473413
0.9111	High Similarity	NPC99572
0.9111	High Similarity	NPC112246
0.9111	High Similarity	NPC126409
0.9104	High Similarity	NPC85435
0.9098	High Similarity	NPC196765
0.9098	High Similarity	NPC469625
0.9098	High Similarity	NPC17343
0.9098	High Similarity	NPC206224
0.9098	High Similarity	NPC129784
0.9098	High Similarity	NPC207892
0.9098	High Similarity	NPC476166
0.9098	High Similarity	NPC118114
0.9098	High Similarity	NPC228369
0.9098	High Similarity	NPC164574
0.9098	High Similarity	NPC30043
0.9098	High Similarity	NPC268917
0.9098	High Similarity	NPC469613
0.9098	High Similarity	NPC236014
0.9098	High Similarity	NPC129106
0.9098	High Similarity	NPC472597
0.9098	High Similarity	NPC12875
0.9098	High Similarity	NPC150011
0.9098	High Similarity	NPC280653
0.9098	High Similarity	NPC300875
0.9098	High Similarity	NPC474017
0.9091	High Similarity	NPC469963
0.9091	High Similarity	NPC469951
0.9084	High Similarity	NPC474119
0.9078	High Similarity	NPC320970
0.9078	High Similarity	NPC320671
0.9078	High Similarity	NPC328567
0.9078	High Similarity	NPC327412
0.9065	High Similarity	NPC258083
0.9065	High Similarity	NPC474104
0.9051	High Similarity	NPC25966
0.9051	High Similarity	NPC32630
0.9051	High Similarity	NPC127218
0.9051	High Similarity	NPC475836
0.9051	High Similarity	NPC319647
0.9051	High Similarity	NPC245207
0.9044	High Similarity	NPC230734
0.9044	High Similarity	NPC269091
0.9044	High Similarity	NPC172818
0.9044	High Similarity	NPC327735
0.9044	High Similarity	NPC25695
0.9044	High Similarity	NPC474639
0.9044	High Similarity	NPC227503
0.9044	High Similarity	NPC302701
0.9044	High Similarity	NPC126101
0.9037	High Similarity	NPC124085
0.9037	High Similarity	NPC117048
0.9037	High Similarity	NPC317380
0.9037	High Similarity	NPC478085
0.903	High Similarity	NPC184447
0.903	High Similarity	NPC470752
0.903	High Similarity	NPC16208
0.903	High Similarity	NPC13005
0.903	High Similarity	NPC160991
0.903	High Similarity	NPC7903
0.903	High Similarity	NPC35932
0.9023	High Similarity	NPC77040
0.9023	High Similarity	NPC242807
0.9023	High Similarity	NPC192687
0.9023	High Similarity	NPC174495
0.9023	High Similarity	NPC237169
0.9023	High Similarity	NPC153739
0.9023	High Similarity	NPC224157
0.9023	High Similarity	NPC470624
0.9023	High Similarity	NPC145305
0.9023	High Similarity	NPC469614
0.9023	High Similarity	NPC42300
0.9023	High Similarity	NPC470225
0.9023	High Similarity	NPC469612
0.9023	High Similarity	NPC241522
0.9023	High Similarity	NPC257582
0.9023	High Similarity	NPC27187
0.9023	High Similarity	NPC472338
0.9023	High Similarity	NPC92164
0.9023	High Similarity	NPC187998
0.9023	High Similarity	NPC64201
0.9021	High Similarity	NPC472710
0.9021	High Similarity	NPC472709
0.9015	High Similarity	NPC31707
0.9015	High Similarity	NPC222127
0.9015	High Similarity	NPC82862

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 NPC477938 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	862
0.2-0.3	1816
0.3-0.4	2679
0.4-0.5	1639
0.5-0.6	953
0.6-0.7	650
0.7-0.8	200
0.8-0.85	12
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8947	High Similarity	NPD3027	Phase 3
0.8889	High Similarity	NPD1613	Approved
0.8889	High Similarity	NPD1612	Clinical (unspecified phase)
0.8603	High Similarity	NPD4907	Clinical (unspecified phase)
0.8593	High Similarity	NPD1529	Clinical (unspecified phase)
0.8519	High Similarity	NPD1530	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD4908	Phase 1
0.8346	Intermediate Similarity	NPD1610	Phase 2
0.8248	Intermediate Similarity	NPD2861	Phase 2
0.8212	Intermediate Similarity	NPD37	Approved
0.817	Intermediate Similarity	NPD4967	Phase 2
0.817	Intermediate Similarity	NPD4966	Approved
0.817	Intermediate Similarity	NPD4965	Approved
0.8129	Intermediate Similarity	NPD4625	Phase 3
0.8116	Intermediate Similarity	NPD3018	Phase 2
0.8077	Intermediate Similarity	NPD5283	Phase 1
0.8071	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD1548	Phase 1
0.8039	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD6674	Discontinued
0.8014	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD5494	Approved
0.7974	Intermediate Similarity	NPD1934	Approved
0.7962	Intermediate Similarity	NPD7199	Phase 2
0.7958	Intermediate Similarity	NPD4060	Phase 1
0.7956	Intermediate Similarity	NPD4749	Approved
0.7956	Intermediate Similarity	NPD2982	Phase 2
0.7956	Intermediate Similarity	NPD2983	Phase 2
0.7949	Intermediate Similarity	NPD6234	Discontinued
0.7914	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD5844	Phase 1
0.7883	Intermediate Similarity	NPD2981	Phase 2
0.7821	Intermediate Similarity	NPD3882	Suspended
0.781	Intermediate Similarity	NPD3705	Approved
0.7778	Intermediate Similarity	NPD5124	Phase 1
0.7778	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD8651	Approved
0.7756	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5588	Approved
0.7718	Intermediate Similarity	NPD3892	Phase 2
0.7718	Intermediate Similarity	NPD6331	Phase 2
0.7716	Intermediate Similarity	NPD3818	Discontinued
0.7716	Intermediate Similarity	NPD7228	Approved
0.7712	Intermediate Similarity	NPD1653	Approved
0.7708	Intermediate Similarity	NPD3620	Phase 2
0.7708	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD6166	Phase 2
0.7698	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2801	Approved
0.7681	Intermediate Similarity	NPD1091	Approved
0.7671	Intermediate Similarity	NPD4538	Approved
0.7671	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4536	Approved
0.7667	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD5762	Approved
0.7635	Intermediate Similarity	NPD5763	Approved
0.7616	Intermediate Similarity	NPD5058	Phase 3
0.7613	Intermediate Similarity	NPD4678	Approved
0.7613	Intermediate Similarity	NPD4675	Approved
0.7595	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD1357	Approved
0.7557	Intermediate Similarity	NPD2684	Approved
0.7556	Intermediate Similarity	NPD7157	Approved
0.7534	Intermediate Similarity	NPD5735	Approved
0.7534	Intermediate Similarity	NPD6355	Discontinued
0.7533	Intermediate Similarity	NPD4236	Phase 3
0.7533	Intermediate Similarity	NPD4237	Approved
0.7533	Intermediate Similarity	NPD5177	Phase 3
0.7532	Intermediate Similarity	NPD2563	Approved
0.7532	Intermediate Similarity	NPD3817	Phase 2
0.7532	Intermediate Similarity	NPD2560	Approved
0.7519	Intermediate Similarity	NPD228	Approved
0.7518	Intermediate Similarity	NPD6696	Suspended
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	NPD3540	Phase 1
0.7517	Intermediate Similarity	NPD6005	Phase 3
0.7517	Intermediate Similarity	NPD6002	Phase 3
0.7516	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD5960	Phase 3
0.7483	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4110	Phase 3
0.7481	Intermediate Similarity	NPD290	Approved
0.7469	Intermediate Similarity	NPD7229	Phase 3
0.7469	Intermediate Similarity	NPD6232	Discontinued
0.7468	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD2424	Discontinued
0.7466	Intermediate Similarity	NPD2238	Phase 2
0.7463	Intermediate Similarity	NPD7843	Approved
0.7455	Intermediate Similarity	NPD7054	Approved
0.7452	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1511	Approved
0.745	Intermediate Similarity	NPD3539	Phase 1
0.7439	Intermediate Similarity	NPD7473	Discontinued
0.7436	Intermediate Similarity	NPD4005	Discontinued
0.7434	Intermediate Similarity	NPD2677	Approved
0.7429	Intermediate Similarity	NPD422	Phase 1
0.7426	Intermediate Similarity	NPD6671	Approved
0.7425	Intermediate Similarity	NPD6559	Discontinued
0.7425	Intermediate Similarity	NPD7240	Approved
0.7423	Intermediate Similarity	NPD2970	Approved
0.7423	Intermediate Similarity	NPD2969	Approved
0.7421	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1652	Phase 2
0.741	Intermediate Similarity	NPD7472	Approved
0.7403	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1375	Discontinued
0.7386	Intermediate Similarity	NPD7124	Phase 2
0.7383	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7549	Discontinued
0.7368	Intermediate Similarity	NPD3022	Approved
0.7368	Intermediate Similarity	NPD3021	Approved
0.7368	Intermediate Similarity	NPD7466	Approved
0.7362	Intermediate Similarity	NPD3051	Approved
0.7358	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7819	Suspended
0.7355	Intermediate Similarity	NPD1512	Approved
0.7347	Intermediate Similarity	NPD1558	Phase 1
0.7347	Intermediate Similarity	NPD4140	Approved
0.7338	Intermediate Similarity	NPD4357	Discontinued
0.7338	Intermediate Similarity	NPD7213	Phase 3
0.7338	Intermediate Similarity	NPD7212	Phase 2
0.7338	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6100	Approved
0.7333	Intermediate Similarity	NPD6099	Approved
0.7333	Intermediate Similarity	NPD2161	Phase 2
0.7329	Intermediate Similarity	NPD7075	Discontinued
0.7324	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD5327	Phase 3
0.7303	Intermediate Similarity	NPD3060	Approved
0.7301	Intermediate Similarity	NPD8127	Discontinued
0.7301	Intermediate Similarity	NPD1247	Approved
0.7296	Intermediate Similarity	NPD6801	Discontinued
0.729	Intermediate Similarity	NPD4123	Phase 3
0.729	Intermediate Similarity	NPD7447	Phase 1
0.7285	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD919	Approved
0.7278	Intermediate Similarity	NPD7808	Phase 3
0.7273	Intermediate Similarity	NPD6666	Approved
0.7273	Intermediate Similarity	NPD2489	Approved
0.7273	Intermediate Similarity	NPD6667	Approved
0.7273	Intermediate Similarity	NPD27	Approved
0.7267	Intermediate Similarity	NPD7033	Discontinued
0.7262	Intermediate Similarity	NPD6797	Phase 2
0.7256	Intermediate Similarity	NPD6071	Discontinued
0.7255	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4628	Phase 3
0.7254	Intermediate Similarity	NPD2235	Phase 2
0.7254	Intermediate Similarity	NPD2231	Phase 2
0.725	Intermediate Similarity	NPD5773	Approved
0.725	Intermediate Similarity	NPD5772	Approved
0.7248	Intermediate Similarity	NPD2157	Approved
0.7248	Intermediate Similarity	NPD6653	Approved
0.7248	Intermediate Similarity	NPD4097	Suspended
0.7244	Intermediate Similarity	NPD7526	Approved
0.7244	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD52	Approved
0.7239	Intermediate Similarity	NPD4750	Phase 3
0.7237	Intermediate Similarity	NPD1549	Phase 2
0.7233	Intermediate Similarity	NPD6072	Discontinued
0.7222	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7251	Discontinued
0.7219	Intermediate Similarity	NPD2796	Approved
0.7212	Intermediate Similarity	NPD3926	Phase 2
0.7211	Intermediate Similarity	NPD6798	Discontinued
0.7209	Intermediate Similarity	NPD4663	Approved
0.72	Intermediate Similarity	NPD6111	Discontinued
0.7197	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5976	Discontinued
0.7195	Intermediate Similarity	NPD6959	Discontinued
0.7194	Intermediate Similarity	NPD5536	Phase 2
0.7192	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4162	Approved
0.7181	Intermediate Similarity	NPD3657	Discovery
0.7179	Intermediate Similarity	NPD2533	Approved
0.7179	Intermediate Similarity	NPD2534	Approved
0.7179	Intermediate Similarity	NPD2532	Approved
0.7176	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3691	Phase 2
0.7172	Intermediate Similarity	NPD6584	Phase 3
0.7172	Intermediate Similarity	NPD3690	Phase 2
0.7171	Intermediate Similarity	NPD7266	Discontinued
0.7171	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5846	Approved
0.7163	Intermediate Similarity	NPD5125	Phase 3
0.7163	Intermediate Similarity	NPD5126	Approved
0.7163	Intermediate Similarity	NPD6516	Phase 2
0.7163	Intermediate Similarity	NPD4626	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