NPASS Compound

Structure

NPC269886 OpenBabel07101718222D 26 29 0 0 1 0 0 0 0 0999 V2000 -2.9715 -1.5099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1123 2.0240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3436 3.0658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2777 -0.7896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6582 2.0161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6582 -0.3981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9414 0.7192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5546 0.1713 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 -3.3653 0.3090 0.0000 C 0 0 2 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 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6582 2.0161 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6582 -0.3981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3653 1.3090 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 -4.2891 1.6917 0.0000 C 0 0 0 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 -1.9875 1.5403 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2755 -1.3220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0825 1.0829 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4197 2.6831 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 23 1 0 0 0 0 3 26 1 0 0 0 0 4 12 2 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 13 2 0 0 0 0 8 16 2 0 0 0 0 9 15 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 10 1 1 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 16 22 1 0 0 0 0 17 9 1 6 0 0 0 17 19 1 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 18 24 2 0 0 0 0 19 21 1 1 0 0 0 20 22 1 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.18
Volume:	367.455
LogP:	3.122
LogD:	2.943
LogS:	-3.709
# Rotatable Bonds:	2
TPSA:	62.4
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.633
Synthetic Accessibility Score:	4.575
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.793
MDCK Permeability:	3.250923691666685e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.974
Plasma Protein Binding (PPB):	72.54705810546875%
Volume Distribution (VD):	1.928
Pgp-substrate:	39.80870819091797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.812
CYP1A2-substrate:	0.564
CYP2C19-inhibitor:	0.492
CYP2C19-substrate:	0.884
CYP2C9-inhibitor:	0.138
CYP2C9-substrate:	0.262
CYP2D6-inhibitor:	0.645
CYP2D6-substrate:	0.877
CYP3A4-inhibitor:	0.659
CYP3A4-substrate:	0.788

ADMET: Excretion

Clearance (CL):	12.307
Half-life (T1/2):	0.2

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.225
Drug-inuced Liver Injury (DILI):	0.523
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.972
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.559
Carcinogencity:	0.821
Eye Corrosion:	0.018
Eye Irritation:	0.02
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC269886

Natural Product ID:	NPC269886
*Common Name:**	TYPMTMPLTVSOBU-AGAZHLLFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TYPMTMPLTVSOBU-AGAZHLLFSA-N
Standard InCHI:	InChI=1S/C21H24N2O3/c1-4-12-11-23(2)17-9-15-13-7-5-6-8-16(13)22-20(15)18(24)10-14(12)19(17)21(25)26-3/h4-8,14,17,19,22H,9-11H2,1-3H3/b12-4-/t14-,17+,19-/m1/s1
SMILES:	C/C=C1/CN(C)[C@H]2Cc3c4ccccc4[nH]c3C(=O)C[C@H]1[C@H]2C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3358049
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002744] Vobasan alkaloids

*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
NPO32666	tabernaemontana	Genus	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25333996]

☑ 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	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	5.6	ug.mL-1	PMID[453272]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	22.0	ug.mL-1	PMID[453272]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13.5	ug.mL-1	PMID[453272]

☑ 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 NPC269886 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	313
0.1-0.2	1975
0.2-0.3	11396
0.3-0.4	19111
0.4-0.5	5109
0.5-0.6	2203
0.6-0.7	1995
0.7-0.8	526
0.8-0.85	57
0.85-0.9	3
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472210
1.0	High Similarity	NPC81802
1.0	High Similarity	NPC247735
1.0	High Similarity	NPC472295
0.9598	High Similarity	NPC472292
0.9435	High Similarity	NPC472293
0.9278	High Similarity	NPC472296
0.9278	High Similarity	NPC472297
0.9048	High Similarity	NPC472291
0.8596	High Similarity	NPC469896
0.8525	High Similarity	NPC472112
0.8525	High Similarity	NPC314333
0.8525	High Similarity	NPC329858
0.8441	Intermediate Similarity	NPC220151
0.8441	Intermediate Similarity	NPC19692
0.8432	Intermediate Similarity	NPC472113
0.837	Intermediate Similarity	NPC196251
0.837	Intermediate Similarity	NPC111602
0.837	Intermediate Similarity	NPC102338
0.837	Intermediate Similarity	NPC63199
0.8333	Intermediate Similarity	NPC55493
0.8333	Intermediate Similarity	NPC219336
0.8298	Intermediate Similarity	NPC472116
0.8278	Intermediate Similarity	NPC15573
0.8278	Intermediate Similarity	NPC183662
0.8278	Intermediate Similarity	NPC217372
0.827	Intermediate Similarity	NPC175474
0.822	Intermediate Similarity	NPC312870
0.822	Intermediate Similarity	NPC254240
0.822	Intermediate Similarity	NPC128265
0.822	Intermediate Similarity	NPC199851
0.822	Intermediate Similarity	NPC294909
0.8211	Intermediate Similarity	NPC52557
0.8201	Intermediate Similarity	NPC245916
0.8177	Intermediate Similarity	NPC14113
0.8177	Intermediate Similarity	NPC145885
0.8177	Intermediate Similarity	NPC84827
0.8135	Intermediate Similarity	NPC162730
0.8105	Intermediate Similarity	NPC102592
0.8105	Intermediate Similarity	NPC79356
0.8079	Intermediate Similarity	NPC21174
0.8079	Intermediate Similarity	NPC271797
0.8073	Intermediate Similarity	NPC241024
0.8054	Intermediate Similarity	NPC258480
0.8051	Intermediate Similarity	NPC132539
0.8041	Intermediate Similarity	NPC474116
0.8031	Intermediate Similarity	NPC249150
0.8031	Intermediate Similarity	NPC81654
0.8031	Intermediate Similarity	NPC79129
0.8031	Intermediate Similarity	NPC49196
0.8031	Intermediate Similarity	NPC214428
0.8031	Intermediate Similarity	NPC195461
0.8031	Intermediate Similarity	NPC313985
0.8021	Intermediate Similarity	NPC472323
0.8011	Intermediate Similarity	NPC133003
0.8	Intermediate Similarity	NPC143533
0.7989	Intermediate Similarity	NPC15840
0.7978	Intermediate Similarity	NPC234987
0.797	Intermediate Similarity	NPC477065
0.7968	Intermediate Similarity	NPC235684
0.7968	Intermediate Similarity	NPC66210
0.7957	Intermediate Similarity	NPC472119
0.7937	Intermediate Similarity	NPC324091
0.7935	Intermediate Similarity	NPC126709
0.7935	Intermediate Similarity	NPC248041
0.7933	Intermediate Similarity	NPC115232
0.7927	Intermediate Similarity	NPC50503
0.7923	Intermediate Similarity	NPC267885
0.7923	Intermediate Similarity	NPC151635
0.7919	Intermediate Similarity	NPC277350
0.7908	Intermediate Similarity	NPC165599
0.7903	Intermediate Similarity	NPC159125
0.7876	Intermediate Similarity	NPC141454
0.7872	Intermediate Similarity	NPC160381
0.7871	Intermediate Similarity	NPC477979
0.7869	Intermediate Similarity	NPC203468
0.7869	Intermediate Similarity	NPC149155
0.7869	Intermediate Similarity	NPC110500
0.7838	Intermediate Similarity	NPC283219
0.7838	Intermediate Similarity	NPC55772
0.7819	Intermediate Similarity	NPC79062
0.7819	Intermediate Similarity	NPC472107
0.7814	Intermediate Similarity	NPC161861
0.7806	Intermediate Similarity	NPC471944
0.7772	Intermediate Similarity	NPC118940
0.7754	Intermediate Similarity	NPC191415
0.7754	Intermediate Similarity	NPC113626
0.775	Intermediate Similarity	NPC266249
0.7747	Intermediate Similarity	NPC78020
0.7722	Intermediate Similarity	NPC214106
0.7717	Intermediate Similarity	NPC252572
0.7714	Intermediate Similarity	NPC478078
0.7711	Intermediate Similarity	NPC469743
0.7707	Intermediate Similarity	NPC312645
0.7704	Intermediate Similarity	NPC74413
0.7701	Intermediate Similarity	NPC91179
0.77	Intermediate Similarity	NPC244741
0.7696	Intermediate Similarity	NPC321708
0.768	Intermediate Similarity	NPC474121
0.7673	Intermediate Similarity	NPC123839
0.7673	Intermediate Similarity	NPC234999
0.7672	Intermediate Similarity	NPC477003
0.7659	Intermediate Similarity	NPC330009
0.7659	Intermediate Similarity	NPC469928
0.7659	Intermediate Similarity	NPC36405
0.7647	Intermediate Similarity	NPC234078
0.7647	Intermediate Similarity	NPC213468
0.7647	Intermediate Similarity	NPC89508
0.7647	Intermediate Similarity	NPC221100
0.7622	Intermediate Similarity	NPC472123
0.7619	Intermediate Similarity	NPC139291
0.7619	Intermediate Similarity	NPC472108
0.7617	Intermediate Similarity	NPC138370
0.7617	Intermediate Similarity	NPC472097
0.7602	Intermediate Similarity	NPC227582
0.7598	Intermediate Similarity	NPC475778
0.7594	Intermediate Similarity	NPC111275
0.7594	Intermediate Similarity	NPC284775
0.7592	Intermediate Similarity	NPC62749
0.759	Intermediate Similarity	NPC289299
0.759	Intermediate Similarity	NPC57994
0.7588	Intermediate Similarity	NPC476874
0.7588	Intermediate Similarity	NPC137589
0.7588	Intermediate Similarity	NPC260900
0.7585	Intermediate Similarity	NPC96321
0.7585	Intermediate Similarity	NPC281049
0.7585	Intermediate Similarity	NPC473041
0.7581	Intermediate Similarity	NPC329688
0.7581	Intermediate Similarity	NPC189812
0.7573	Intermediate Similarity	NPC148183
0.7573	Intermediate Similarity	NPC152768
0.755	Intermediate Similarity	NPC476098
0.754	Intermediate Similarity	NPC84347
0.7538	Intermediate Similarity	NPC267343
0.7526	Intermediate Similarity	NPC470205
0.7526	Intermediate Similarity	NPC476460
0.7526	Intermediate Similarity	NPC102755
0.7525	Intermediate Similarity	NPC270918
0.7514	Intermediate Similarity	NPC471943
0.7513	Intermediate Similarity	NPC221873
0.7513	Intermediate Similarity	NPC262898
0.7512	Intermediate Similarity	NPC185742
0.7512	Intermediate Similarity	NPC475847
0.7512	Intermediate Similarity	NPC311906
0.7512	Intermediate Similarity	NPC33949
0.75	Intermediate Similarity	NPC285469
0.75	Intermediate Similarity	NPC202812
0.7488	Intermediate Similarity	NPC475271
0.7488	Intermediate Similarity	NPC229893
0.7487	Intermediate Similarity	NPC67551
0.7487	Intermediate Similarity	NPC252338
0.7475	Intermediate Similarity	NPC306376
0.7475	Intermediate Similarity	NPC67288
0.7474	Intermediate Similarity	NPC154339
0.7473	Intermediate Similarity	NPC6982
0.7464	Intermediate Similarity	NPC52254
0.7463	Intermediate Similarity	NPC82370
0.7463	Intermediate Similarity	NPC317701
0.7462	Intermediate Similarity	NPC179701
0.7459	Intermediate Similarity	NPC317430
0.7459	Intermediate Similarity	NPC76982
0.7453	Intermediate Similarity	NPC21638
0.7451	Intermediate Similarity	NPC478158
0.744	Intermediate Similarity	NPC474412
0.7437	Intermediate Similarity	NPC81535
0.7435	Intermediate Similarity	NPC19679
0.7435	Intermediate Similarity	NPC472104
0.743	Intermediate Similarity	NPC194740
0.7429	Intermediate Similarity	NPC472099
0.7424	Intermediate Similarity	NPC167710
0.7416	Intermediate Similarity	NPC82070
0.7415	Intermediate Similarity	NPC471304
0.7414	Intermediate Similarity	NPC59084
0.7413	Intermediate Similarity	NPC57398
0.7409	Intermediate Similarity	NPC17273
0.7409	Intermediate Similarity	NPC478077
0.7409	Intermediate Similarity	NPC141612
0.7409	Intermediate Similarity	NPC315555
0.7409	Intermediate Similarity	NPC135601
0.7406	Intermediate Similarity	NPC64216
0.7405	Intermediate Similarity	NPC49954
0.7405	Intermediate Similarity	NPC474561
0.7404	Intermediate Similarity	NPC476114
0.7396	Intermediate Similarity	NPC228835
0.7391	Intermediate Similarity	NPC229348
0.7385	Intermediate Similarity	NPC83111
0.7385	Intermediate Similarity	NPC469470
0.7385	Intermediate Similarity	NPC469501
0.7382	Intermediate Similarity	NPC71037
0.7374	Intermediate Similarity	NPC11445
0.7373	Intermediate Similarity	NPC70155
0.7371	Intermediate Similarity	NPC63157
0.7371	Intermediate Similarity	NPC278434
0.7371	Intermediate Similarity	NPC473868
0.7368	Intermediate Similarity	NPC305984
0.736	Intermediate Similarity	NPC304203
0.736	Intermediate Similarity	NPC88315
0.736	Intermediate Similarity	NPC326422
0.7356	Intermediate Similarity	NPC313640
0.7353	Intermediate Similarity	NPC4687

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 NPC269886 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	524
0.2-0.3	754
0.3-0.4	1709
0.4-0.5	2630
0.5-0.6	2414
0.6-0.7	827
0.7-0.8	103
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8525	High Similarity	NPD4499	Approved
0.822	Intermediate Similarity	NPD4501	Approved
0.822	Intermediate Similarity	NPD4500	Approved
0.8031	Intermediate Similarity	NPD4600	Approved
0.8031	Intermediate Similarity	NPD4601	Approved
0.7921	Intermediate Similarity	NPD3393	Approved
0.7921	Intermediate Similarity	NPD3394	Approved
0.7921	Intermediate Similarity	NPD3389	Approved
0.7903	Intermediate Similarity	NPD2094	Phase 2
0.7903	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD2092	Phase 2
0.7903	Intermediate Similarity	NPD2095	Phase 2
0.7869	Intermediate Similarity	NPD482	Approved
0.7861	Intermediate Similarity	NPD2091	Phase 2
0.7861	Intermediate Similarity	NPD2096	Phase 2
0.7839	Intermediate Similarity	NPD2509	Approved
0.7839	Intermediate Similarity	NPD2510	Approved
0.7826	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD6176	Phase 1
0.7809	Intermediate Similarity	NPD1630	Approved
0.78	Intermediate Similarity	NPD4506	Discontinued
0.7796	Intermediate Similarity	NPD5473	Discontinued
0.7772	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD6770	Approved
0.7717	Intermediate Similarity	NPD750	Phase 2
0.768	Intermediate Similarity	NPD1631	Approved
0.7672	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD1573	Approved
0.7609	Intermediate Similarity	NPD1575	Approved
0.76	Intermediate Similarity	NPD5901	Discontinued
0.7598	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD4602	Approved
0.7586	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD2844	Phase 3
0.7552	Intermediate Similarity	NPD4948	Discontinued
0.7526	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2213	Approved
0.7514	Intermediate Similarity	NPD2214	Approved
0.75	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD1586	Approved
0.7409	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7470	Discontinued
0.7368	Intermediate Similarity	NPD1587	Approved
0.7351	Intermediate Similarity	NPD2915	Discontinued
0.735	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD3319	Phase 1
0.7344	Intermediate Similarity	NPD3318	Approved
0.7344	Intermediate Similarity	NPD3320	Approved
0.734	Intermediate Similarity	NPD8114	Approved
0.734	Intermediate Similarity	NPD8115	Approved
0.734	Intermediate Similarity	NPD4524	Discontinued
0.734	Intermediate Similarity	NPD3947	Discontinued
0.7337	Intermediate Similarity	NPD5003	Discontinued
0.7313	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD8072	Approved
0.7285	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7727	Phase 2
0.7277	Intermediate Similarity	NPD7817	Phase 1
0.7273	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7454	Approved
0.726	Intermediate Similarity	NPD7455	Approved
0.7259	Intermediate Similarity	NPD2336	Approved
0.7259	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5426	Phase 3
0.7245	Intermediate Similarity	NPD1534	Approved
0.7241	Intermediate Similarity	NPD8073	Approved
0.7234	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3178	Discontinued
0.72	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6987	Phase 1
0.7171	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD8098	Approved
0.7169	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6376	Discontinued
0.7143	Intermediate Similarity	NPD5809	Phase 3
0.7143	Intermediate Similarity	NPD484	Approved
0.7136	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7957	Phase 1
0.7129	Intermediate Similarity	NPD4397	Phase 1
0.7129	Intermediate Similarity	NPD5475	Discontinued
0.7121	Intermediate Similarity	NPD2564	Approved
0.7121	Intermediate Similarity	NPD2565	Phase 2
0.7115	Intermediate Similarity	NPD4520	Approved
0.7114	Intermediate Similarity	NPD2307	Discontinued
0.7103	Intermediate Similarity	NPD1996	Discontinued
0.7103	Intermediate Similarity	NPD6242	Discontinued
0.7095	Intermediate Similarity	NPD8097	Phase 3
0.7095	Intermediate Similarity	NPD8096	Phase 3
0.7089	Intermediate Similarity	NPD7878	Phase 2
0.7089	Intermediate Similarity	NPD5632	Approved
0.7083	Intermediate Similarity	NPD5104	Approved
0.7081	Intermediate Similarity	NPD4326	Phase 2
0.7081	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6664	Approved
0.7078	Intermediate Similarity	NPD4952	Phase 3
0.7074	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7619	Phase 3
0.7065	Intermediate Similarity	NPD7618	Phase 3
0.7062	Intermediate Similarity	NPD5897	Approved
0.7062	Intermediate Similarity	NPD5898	Approved
0.7062	Intermediate Similarity	NPD5899	Approved
0.7062	Intermediate Similarity	NPD6595	Phase 3
0.7059	Intermediate Similarity	NPD6479	Discontinued
0.7053	Intermediate Similarity	NPD1326	Approved
0.7053	Intermediate Similarity	NPD1325	Approved
0.7053	Intermediate Similarity	NPD7568	Phase 1
0.7053	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6665	Discontinued
0.7047	Intermediate Similarity	NPD2144	Approved
0.7045	Intermediate Similarity	NPD7688	Phase 1
0.7037	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7941	Phase 3
0.7031	Intermediate Similarity	NPD5482	Discontinued
0.703	Intermediate Similarity	NPD6226	Phase 3
0.703	Intermediate Similarity	NPD4848	Phase 1
0.7028	Intermediate Similarity	NPD5293	Phase 2
0.7026	Intermediate Similarity	NPD3038	Discontinued
0.7022	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6249	Phase 2
0.701	Intermediate Similarity	NPD6999	Discontinued
0.701	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6248	Phase 2
0.7009	Intermediate Similarity	NPD6578	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4463	Approved
0.6995	Remote Similarity	NPD4462	Approved
0.6986	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD4334	Discontinued
0.6983	Remote Similarity	NPD5020	Approved
0.6983	Remote Similarity	NPD1722	Approved
0.6982	Remote Similarity	NPD4373	Phase 2
0.6967	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD53	Approved
0.6961	Remote Similarity	NPD7778	Approved
0.6961	Remote Similarity	NPD7777	Approved
0.6959	Remote Similarity	NPD7865	Approved
0.6954	Remote Similarity	NPD7564	Discontinued
0.6947	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD8358	Approved
0.6943	Remote Similarity	NPD5065	Approved
0.6942	Remote Similarity	NPD5017	Discontinued
0.6939	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4885	Approved
0.6927	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7308	Discontinued
0.6923	Remote Similarity	NPD3077	Approved
0.6923	Remote Similarity	NPD3078	Approved
0.6923	Remote Similarity	NPD3076	Approved
0.6923	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3079	Approved
0.6923	Remote Similarity	NPD8272	Phase 2
0.6923	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.692	Remote Similarity	NPD3006	Discontinued
0.6919	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD8160	Phase 2
0.6909	Remote Similarity	NPD7994	Phase 2
0.6907	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4075	Phase 2
0.6906	Remote Similarity	NPD5254	Discontinued
0.6905	Remote Similarity	NPD6486	Approved
0.6905	Remote Similarity	NPD6487	Approved
0.6905	Remote Similarity	NPD2916	Discontinued
0.6904	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3243	Approved
0.69	Remote Similarity	NPD7234	Approved
0.69	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7233	Approved
0.6897	Remote Similarity	NPD7944	Discontinued
0.6895	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2008	Discontinued
0.689	Remote Similarity	NPD7001	Phase 3
0.6888	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5818	Discontinued
0.6884	Remote Similarity	NPD5444	Phase 1
0.6881	Remote Similarity	NPD5505	Discontinued
0.6881	Remote Similarity	NPD6995	Phase 1
0.6872	Remote Similarity	NPD7869	Discontinued
0.6872	Remote Similarity	NPD786	Approved
0.6869	Remote Similarity	NPD7970	Approved
0.6869	Remote Similarity	NPD7971	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