NPASS Compound

Structure

CID162730 OpenBabel06191715532D 25 29 0 0 1 0 0 0 0 0999 V2000 2.6598 3.3077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2210 0.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6327 1.5199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6327 0.5064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7556 2.0265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7555 -0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2047 1.0379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2617 1.1569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1465 1.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4500 0.4548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3846 -0.3632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6320 1.5203 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8778 1.5200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6321 0.5067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8778 0.5065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8771 1.5201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7548 2.0267 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8772 0.5066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1254 -0.3635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7549 0.0001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5012 2.2568 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3247 -1.0626 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4203 -0.1865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0867 -0.1749 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 24 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 13 2 0 0 0 0 6 15 2 0 0 0 0 7 9 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 9 22 1 0 0 0 0 10 25 1 0 0 0 0 11 20 1 0 0 0 0 11 25 1 0 0 0 0 12 8 1 1 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 20 1 6 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 17 16 1 6 0 0 0 17 22 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 19 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.18
Volume:	346.876
LogP:	2.503
LogD:	2.714
LogS:	-1.993
# Rotatable Bonds:	2
TPSA:	54.56
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.811
Synthetic Accessibility Score:	5.128
Fsp3:	0.55
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:	-4.96
MDCK Permeability:	1.4657727660960518e-05
Pgp-inhibitor:	0.052
Pgp-substrate:	0.62
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.262
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988
Plasma Protein Binding (PPB):	74.25174713134766%
Volume Distribution (VD):	1.747
Pgp-substrate:	35.45009231567383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.29
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.612
CYP2C19-substrate:	0.94
CYP2C9-inhibitor:	0.181
CYP2C9-substrate:	0.366
CYP2D6-inhibitor:	0.337
CYP2D6-substrate:	0.877
CYP3A4-inhibitor:	0.756
CYP3A4-substrate:	0.892

ADMET: Excretion

Clearance (CL):	9.588
Half-life (T1/2):	0.171

ADMET: Toxicity

hERG Blockers:	0.687
Human Hepatotoxicity (H-HT):	0.32
Drug-inuced Liver Injury (DILI):	0.084
AMES Toxicity:	0.652
Rat Oral Acute Toxicity:	0.952
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.143
Carcinogencity:	0.806
Eye Corrosion:	0.004
Eye Irritation:	0.019
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC162730

Natural Product ID:	NPC162730
*Common Name:**	Undulifoline
IUPAC Name:	n.a.
Synonyms:	Undulifoline
Standard InCHIKey:	ITRBOGBMPGNZBO-AJRGADBESA-N
Standard InCHI:	InChI=1S/C20H24N2O3/c1-22-9-7-14-12-8-10-25-11-20(14,19(23)24-2)18-16(17(12)22)13-5-3-4-6-15(13)21-18/h3-6,12,14,17,21H,7-11H2,1-2H3/t12-,14-,17+,20-/m0/s1
SMILES:	COC(=O)[C@@]12COCC[C@H]3[C@@H]1CCN([C@H]3c1c2[nH]c2c1cccc2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459209
PubChem CID:	44561426
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18524603]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19083	Alstonia angustiloba	Species	Apocynaceae	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
Others	1

Activity Type	# Activity
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	33.3	%	PMID[525328]

☑ 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 NPC162730 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	323
0.1-0.2	1639
0.2-0.3	8380
0.3-0.4	22569
0.4-0.5	5095
0.5-0.6	2345
0.6-0.7	1877
0.7-0.8	406
0.8-0.85	43
0.85-0.9	16
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9889	High Similarity	NPC474116
0.9278	High Similarity	NPC329858
0.9149	High Similarity	NPC185742
0.9149	High Similarity	NPC475847
0.9066	High Similarity	NPC314333
0.9016	High Similarity	NPC475778
0.8967	High Similarity	NPC55493
0.8814	High Similarity	NPC234999
0.8684	High Similarity	NPC241024
0.8632	High Similarity	NPC52557
0.8571	High Similarity	NPC469743
0.8542	High Similarity	NPC214428
0.8503	High Similarity	NPC175474
0.8446	Intermediate Similarity	NPC313985
0.8446	Intermediate Similarity	NPC249150
0.8446	Intermediate Similarity	NPC79129
0.8446	Intermediate Similarity	NPC81654
0.8446	Intermediate Similarity	NPC195461
0.8446	Intermediate Similarity	NPC49196
0.8418	Intermediate Similarity	NPC277350
0.8408	Intermediate Similarity	NPC469928
0.8359	Intermediate Similarity	NPC137589
0.8342	Intermediate Similarity	NPC50503
0.8325	Intermediate Similarity	NPC96321
0.8317	Intermediate Similarity	NPC330009
0.8283	Intermediate Similarity	NPC477065
0.8281	Intermediate Similarity	NPC474121
0.8235	Intermediate Similarity	NPC19679
0.8235	Intermediate Similarity	NPC473041
0.8211	Intermediate Similarity	NPC102338
0.8211	Intermediate Similarity	NPC111602
0.8211	Intermediate Similarity	NPC63199
0.8211	Intermediate Similarity	NPC196251
0.8135	Intermediate Similarity	NPC472295
0.8135	Intermediate Similarity	NPC472210
0.8135	Intermediate Similarity	NPC81802
0.8135	Intermediate Similarity	NPC247735
0.8135	Intermediate Similarity	NPC269886
0.8128	Intermediate Similarity	NPC469896
0.8095	Intermediate Similarity	NPC472119
0.8083	Intermediate Similarity	NPC472113
0.8073	Intermediate Similarity	NPC472112
0.8011	Intermediate Similarity	NPC189812
0.8011	Intermediate Similarity	NPC329688
0.8	Intermediate Similarity	NPC220151
0.8	Intermediate Similarity	NPC19692
0.7972	Intermediate Similarity	NPC311906
0.7959	Intermediate Similarity	NPC245916
0.7944	Intermediate Similarity	NPC474192
0.7944	Intermediate Similarity	NPC475720
0.7892	Intermediate Similarity	NPC471304
0.7889	Intermediate Similarity	NPC312870
0.7889	Intermediate Similarity	NPC254240
0.7889	Intermediate Similarity	NPC199851
0.7889	Intermediate Similarity	NPC294909
0.7889	Intermediate Similarity	NPC128265
0.7884	Intermediate Similarity	NPC219336
0.7865	Intermediate Similarity	NPC79062
0.7865	Intermediate Similarity	NPC472107
0.7831	Intermediate Similarity	NPC183662
0.7831	Intermediate Similarity	NPC15573
0.7831	Intermediate Similarity	NPC217372
0.7817	Intermediate Similarity	NPC85066
0.7817	Intermediate Similarity	NPC181502
0.7808	Intermediate Similarity	NPC475816
0.7806	Intermediate Similarity	NPC472292
0.7795	Intermediate Similarity	NPC95783
0.7789	Intermediate Similarity	NPC213468
0.7778	Intermediate Similarity	NPC472291
0.7757	Intermediate Similarity	NPC469720
0.7742	Intermediate Similarity	NPC473105
0.7737	Intermediate Similarity	NPC234987
0.7732	Intermediate Similarity	NPC160381
0.7701	Intermediate Similarity	NPC317430
0.7692	Intermediate Similarity	NPC472323
0.7688	Intermediate Similarity	NPC472293
0.7676	Intermediate Similarity	NPC282339
0.7676	Intermediate Similarity	NPC99632
0.7668	Intermediate Similarity	NPC139291
0.7668	Intermediate Similarity	NPC143533
0.7668	Intermediate Similarity	NPC472108
0.7662	Intermediate Similarity	NPC472297
0.7662	Intermediate Similarity	NPC472296
0.7658	Intermediate Similarity	NPC473540
0.7656	Intermediate Similarity	NPC15840
0.7644	Intermediate Similarity	NPC111275
0.7644	Intermediate Similarity	NPC145885
0.7644	Intermediate Similarity	NPC14113
0.7644	Intermediate Similarity	NPC84827
0.7641	Intermediate Similarity	NPC66210
0.7634	Intermediate Similarity	NPC271797
0.7634	Intermediate Similarity	NPC21174
0.7632	Intermediate Similarity	NPC478080
0.7629	Intermediate Similarity	NPC258480
0.7624	Intermediate Similarity	NPC33421
0.7619	Intermediate Similarity	NPC152768
0.7619	Intermediate Similarity	NPC148183
0.76	Intermediate Similarity	NPC17437
0.7579	Intermediate Similarity	NPC472123
0.7576	Intermediate Similarity	NPC472097
0.7571	Intermediate Similarity	NPC474412
0.7549	Intermediate Similarity	NPC476874
0.7548	Intermediate Similarity	NPC126066
0.7534	Intermediate Similarity	NPC477066
0.7526	Intermediate Similarity	NPC71037
0.7526	Intermediate Similarity	NPC113626
0.7525	Intermediate Similarity	NPC67288
0.7524	Intermediate Similarity	NPC18661
0.7512	Intermediate Similarity	NPC478078
0.7511	Intermediate Similarity	NPC81939
0.75	Intermediate Similarity	NPC477067
0.75	Intermediate Similarity	NPC478081
0.75	Intermediate Similarity	NPC267885
0.75	Intermediate Similarity	NPC478082
0.7487	Intermediate Similarity	NPC16667
0.7487	Intermediate Similarity	NPC472104
0.7478	Intermediate Similarity	NPC475666
0.7474	Intermediate Similarity	NPC280548
0.7465	Intermediate Similarity	NPC281049
0.7463	Intermediate Similarity	NPC289299
0.7463	Intermediate Similarity	NPC57994
0.7463	Intermediate Similarity	NPC193761
0.7463	Intermediate Similarity	NPC260900
0.7462	Intermediate Similarity	NPC62749
0.7462	Intermediate Similarity	NPC315555
0.7462	Intermediate Similarity	NPC235684
0.7462	Intermediate Similarity	NPC99428
0.7459	Intermediate Similarity	NPC285469
0.7451	Intermediate Similarity	NPC329747
0.7448	Intermediate Similarity	NPC203468
0.7448	Intermediate Similarity	NPC149155
0.7448	Intermediate Similarity	NPC110500
0.7437	Intermediate Similarity	NPC469470
0.7437	Intermediate Similarity	NPC469501
0.7435	Intermediate Similarity	NPC126492
0.743	Intermediate Similarity	NPC52254
0.7426	Intermediate Similarity	NPC472116
0.7426	Intermediate Similarity	NPC11445
0.7423	Intermediate Similarity	NPC126709
0.7423	Intermediate Similarity	NPC248041
0.7421	Intermediate Similarity	NPC154293
0.7421	Intermediate Similarity	NPC78020
0.7419	Intermediate Similarity	NPC235885
0.7418	Intermediate Similarity	NPC21605
0.7413	Intermediate Similarity	NPC88315
0.7411	Intermediate Similarity	NPC52262
0.7407	Intermediate Similarity	NPC470508
0.7406	Intermediate Similarity	NPC478157
0.7398	Intermediate Similarity	NPC472109
0.7398	Intermediate Similarity	NPC472110
0.7397	Intermediate Similarity	NPC33949
0.7396	Intermediate Similarity	NPC161861
0.7395	Intermediate Similarity	NPC472099
0.7387	Intermediate Similarity	NPC321708
0.7383	Intermediate Similarity	NPC82070
0.7381	Intermediate Similarity	NPC475422
0.7379	Intermediate Similarity	NPC476073
0.7376	Intermediate Similarity	NPC195239
0.7376	Intermediate Similarity	NPC157828
0.7371	Intermediate Similarity	NPC476114
0.7371	Intermediate Similarity	NPC251936
0.7368	Intermediate Similarity	NPC87755
0.7366	Intermediate Similarity	NPC329793
0.7361	Intermediate Similarity	NPC2395
0.736	Intermediate Similarity	NPC472294
0.7358	Intermediate Similarity	NPC475602
0.7358	Intermediate Similarity	NPC234078
0.7358	Intermediate Similarity	NPC221100
0.7358	Intermediate Similarity	NPC229348
0.7344	Intermediate Similarity	NPC6982
0.7343	Intermediate Similarity	NPC477135
0.7343	Intermediate Similarity	NPC476098
0.7343	Intermediate Similarity	NPC98715
0.7342	Intermediate Similarity	NPC70155
0.734	Intermediate Similarity	NPC225319
0.734	Intermediate Similarity	NPC255229
0.734	Intermediate Similarity	NPC81229
0.7339	Intermediate Similarity	NPC21638
0.7333	Intermediate Similarity	NPC271862
0.7333	Intermediate Similarity	NPC478158
0.7333	Intermediate Similarity	NPC283219
0.7333	Intermediate Similarity	NPC55772
0.7333	Intermediate Similarity	NPC473868
0.7333	Intermediate Similarity	NPC63157
0.7327	Intermediate Similarity	NPC45850
0.7323	Intermediate Similarity	NPC133003
0.7317	Intermediate Similarity	NPC74413
0.7312	Intermediate Similarity	NPC473297
0.7312	Intermediate Similarity	NPC207726
0.7311	Intermediate Similarity	NPC118940
0.7311	Intermediate Similarity	NPC472098
0.731	Intermediate Similarity	NPC159125
0.731	Intermediate Similarity	NPC469358
0.7308	Intermediate Similarity	NPC314648
0.7306	Intermediate Similarity	NPC472762
0.7306	Intermediate Similarity	NPC34508
0.7296	Intermediate Similarity	NPC91179
0.7294	Intermediate Similarity	NPC475271
0.7291	Intermediate Similarity	NPC276517
0.729	Intermediate Similarity	NPC203614

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 NPC162730 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	505
0.2-0.3	714
0.3-0.4	1791
0.4-0.5	2817
0.5-0.6	2354
0.6-0.7	696
0.7-0.8	76
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9066	High Similarity	NPD4499	Approved
0.8446	Intermediate Similarity	NPD4600	Approved
0.8446	Intermediate Similarity	NPD4601	Approved
0.8125	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.799	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD5003	Discontinued
0.7889	Intermediate Similarity	NPD4501	Approved
0.7889	Intermediate Similarity	NPD4500	Approved
0.7789	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD6176	Phase 1
0.7614	Intermediate Similarity	NPD2565	Phase 2
0.7614	Intermediate Similarity	NPD2564	Approved
0.7606	Intermediate Similarity	NPD2844	Phase 3
0.76	Intermediate Similarity	NPD8358	Approved
0.7594	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5426	Phase 3
0.7561	Intermediate Similarity	NPD5901	Discontinued
0.7536	Intermediate Similarity	NPD2509	Approved
0.7536	Intermediate Similarity	NPD2510	Approved
0.7524	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD6770	Approved
0.7512	Intermediate Similarity	NPD2920	Discontinued
0.7488	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD2094	Phase 2
0.7487	Intermediate Similarity	NPD2095	Phase 2
0.7487	Intermediate Similarity	NPD2092	Phase 2
0.7487	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7454	Approved
0.7476	Intermediate Similarity	NPD7455	Approved
0.7475	Intermediate Similarity	NPD1534	Approved
0.7475	Intermediate Similarity	NPD6664	Approved
0.7474	Intermediate Similarity	NPD5473	Discontinued
0.7463	Intermediate Similarity	NPD4602	Approved
0.7453	Intermediate Similarity	NPD3394	Approved
0.7453	Intermediate Similarity	NPD3389	Approved
0.7453	Intermediate Similarity	NPD3393	Approved
0.7449	Intermediate Similarity	NPD2096	Phase 2
0.7449	Intermediate Similarity	NPD2091	Phase 2
0.7448	Intermediate Similarity	NPD482	Approved
0.7409	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD1326	Approved
0.7382	Intermediate Similarity	NPD1325	Approved
0.7368	Intermediate Similarity	NPD2916	Discontinued
0.7353	Intermediate Similarity	NPD4397	Phase 1
0.7352	Intermediate Similarity	NPD6292	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7470	Discontinued
0.7337	Intermediate Similarity	NPD4948	Discontinued
0.7333	Intermediate Similarity	NPD4506	Discontinued
0.7313	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD5913	Phase 3
0.7311	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6987	Phase 1
0.7306	Intermediate Similarity	NPD750	Phase 2
0.73	Intermediate Similarity	NPD7234	Approved
0.73	Intermediate Similarity	NPD7233	Approved
0.7273	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7778	Approved
0.7268	Intermediate Similarity	NPD7777	Approved
0.7268	Intermediate Similarity	NPD53	Approved
0.7264	Intermediate Similarity	NPD5475	Discontinued
0.7245	Intermediate Similarity	NPD4079	Approved
0.7245	Intermediate Similarity	NPD4076	Approved
0.7243	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD4075	Phase 2
0.7225	Intermediate Similarity	NPD3947	Discontinued
0.7222	Intermediate Similarity	NPD7878	Phase 2
0.7222	Intermediate Similarity	NPD3319	Phase 1
0.7222	Intermediate Similarity	NPD3318	Approved
0.7222	Intermediate Similarity	NPD3320	Approved
0.7217	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4334	Discontinued
0.7194	Intermediate Similarity	NPD3505	Approved
0.7194	Intermediate Similarity	NPD3506	Approved
0.719	Intermediate Similarity	NPD7010	Phase 3
0.7183	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD8072	Approved
0.7175	Intermediate Similarity	NPD7688	Phase 1
0.7171	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6995	Phase 1
0.7163	Intermediate Similarity	NPD5293	Phase 2
0.715	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7824	Approved
0.7123	Intermediate Similarity	NPD6376	Discontinued
0.7122	Intermediate Similarity	NPD7618	Phase 3
0.7122	Intermediate Similarity	NPD7619	Phase 3
0.7115	Intermediate Similarity	NPD6479	Discontinued
0.7109	Intermediate Similarity	NPD7957	Phase 1
0.7109	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD8467	Approved
0.7102	Intermediate Similarity	NPD8465	Approved
0.7102	Intermediate Similarity	NPD8466	Approved
0.7094	Intermediate Similarity	NPD6281	Approved
0.7092	Intermediate Similarity	NPD5065	Approved
0.7091	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7955	Approved
0.7089	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7956	Approved
0.7083	Intermediate Similarity	NPD3323	Discontinued
0.7071	Intermediate Similarity	NPD8386	Phase 2
0.707	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6248	Phase 2
0.7067	Intermediate Similarity	NPD6249	Phase 2
0.7067	Intermediate Similarity	NPD6999	Discontinued
0.7067	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5254	Discontinued
0.7062	Intermediate Similarity	NPD8098	Approved
0.7062	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7708	Approved
0.7048	Intermediate Similarity	NPD5891	Approved
0.704	Intermediate Similarity	NPD7731	Approved
0.704	Intermediate Similarity	NPD7730	Approved
0.7039	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8094	Discontinued
0.7035	Intermediate Similarity	NPD7951	Approved
0.7035	Intermediate Similarity	NPD5897	Approved
0.7035	Intermediate Similarity	NPD7953	Approved
0.7035	Intermediate Similarity	NPD7791	Approved
0.7035	Intermediate Similarity	NPD7790	Approved
0.7035	Intermediate Similarity	NPD5899	Approved
0.7035	Intermediate Similarity	NPD7950	Approved
0.7035	Intermediate Similarity	NPD7952	Approved
0.7035	Intermediate Similarity	NPD5898	Approved
0.7035	Intermediate Similarity	NPD7789	Approved
0.703	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7271	Approved
0.7024	Intermediate Similarity	NPD4315	Phase 2
0.702	Intermediate Similarity	NPD2144	Approved
0.7016	Intermediate Similarity	NPD2214	Approved
0.7016	Intermediate Similarity	NPD2213	Approved
0.7012	Intermediate Similarity	NPD7803	Approved
0.7009	Intermediate Similarity	NPD4520	Approved
0.7	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3038	Discontinued
0.6996	Remote Similarity	NPD8364	Approved
0.6996	Remote Similarity	NPD8363	Approved
0.6995	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD8093	Discontinued
0.699	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD8459	Approved
0.6988	Remote Similarity	NPD8460	Approved
0.6988	Remote Similarity	NPD8426	Approved
0.6988	Remote Similarity	NPD8425	Approved
0.6986	Remote Similarity	NPD5632	Approved
0.6977	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD2336	Approved
0.6967	Remote Similarity	NPD8073	Approved
0.6965	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD5596	Phase 2
0.6964	Remote Similarity	NPD8427	Approved
0.6964	Remote Similarity	NPD8429	Approved
0.6964	Remote Similarity	NPD8428	Approved
0.6963	Remote Similarity	NPD8423	Phase 2
0.6963	Remote Similarity	NPD8399	Phase 1
0.6952	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD484	Approved
0.695	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7001	Phase 3
0.6946	Remote Similarity	NPD5444	Phase 1
0.6944	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4181	Approved
0.6927	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD1630	Approved
0.6919	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4885	Approved
0.6912	Remote Similarity	NPD8431	Approved
0.6912	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD3610	Approved
0.6904	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD3609	Approved
0.6902	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8283	Approved
0.6901	Remote Similarity	NPD7103	Approved
0.6901	Remote Similarity	NPD56	Approved
0.6901	Remote Similarity	NPD8282	Approved
0.6898	Remote Similarity	NPD1683	Approved
0.6889	Remote Similarity	NPD6165	Phase 2
0.6889	Remote Similarity	NPD6164	Phase 2
0.6888	Remote Similarity	NPD5021	Discontinued
0.6888	Remote Similarity	NPD4638	Approved
0.6888	Remote Similarity	NPD4640	Approved
0.6888	Remote Similarity	NPD4639	Approved
0.6884	Remote Similarity	NPD5104	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