NPASS Compound

Structure

NPC472116 OpenBabel07101719132D 25 29 0 0 1 0 0 0 0 0999 V2000 1.5702 -1.7739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.8573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8162 -1.1727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8352 -0.4996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2684 -1.2797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4430 0.3814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3093 -1.1789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6703 0.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3458 0.1996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1508 0.4984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9599 -0.2191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4839 0.4822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6703 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9171 -0.2980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8351 1.4465 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7545 0.6592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9171 1.2623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8351 -0.4822 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8351 -2.4108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2902 0.9409 0.0000 N 0 0 3 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 -1.4352 -0.0238 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6703 -2.8930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.8930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 25 1 0 0 0 0 3 11 2 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 12 2 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 16 1 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 8 1 6 0 0 0 13 18 1 0 0 0 0 14 22 1 0 0 0 0 15 19 1 0 0 0 0 15 21 1 1 0 0 0 16 17 1 0 0 0 0 16 23 2 0 0 0 0 17 19 2 0 0 0 0 18 20 1 1 0 0 0 18 22 1 0 0 0 0 19 22 1 0 0 0 0 20 24 2 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.15
Volume:	341.603
LogP:	2.393
LogD:	2.251
LogS:	-2.762
# Rotatable Bonds:	2
TPSA:	51.54
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.593
Synthetic Accessibility Score:	4.802
Fsp3:	0.4
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:	-4.659
MDCK Permeability:	4.582704423228279e-05
Pgp-inhibitor:	0.036
Pgp-substrate:	0.163
Human Intestinal Absorption (HIA):	0.483
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.065

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.94
Plasma Protein Binding (PPB):	74.3311538696289%
Volume Distribution (VD):	1.982
Pgp-substrate:	36.081817626953125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.502
CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.918
CYP2C19-substrate:	0.846
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.313
CYP2D6-inhibitor:	0.075
CYP2D6-substrate:	0.291
CYP3A4-inhibitor:	0.838
CYP3A4-substrate:	0.744

ADMET: Excretion

Clearance (CL):	13.16
Half-life (T1/2):	0.105

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.797
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.282
Rat Oral Acute Toxicity:	0.769
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.152
Carcinogencity:	0.956
Eye Corrosion:	0.003
Eye Irritation:	0.017
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: NPC472116

Natural Product ID:	NPC472116
*Common Name:**	HRMWXBDXMIISES-LRTFYCIKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HRMWXBDXMIISES-LRTFYCIKSA-N
Standard InCHI:	InChI=1S/C20H20N2O3/c1-3-11-9-21-10-16(23)17-12-6-4-5-7-14(12)22-18(20(24)25-2)13(11)8-15(21)19(17)22/h3-7,13,15,18H,8-10H2,1-2H3/b11-3-/t13-,15-,18-/m0/s1
SMILES:	CC=C1CN2CC(=O)C3=C4C2CC1C(N4C5=CC=CC=C53)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338239
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003762] Pleiocarpaman 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
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	bark and leaf	Pahang, Malaysia	n.a.	PMID[25211145]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28762	Alstonia angustifolia	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
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[567769]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[567769]

☑ 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 NPC472116 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	319
0.1-0.2	1894
0.2-0.3	11289
0.3-0.4	19711
0.4-0.5	4372
0.5-0.6	2571
0.6-0.7	1998
0.7-0.8	494
0.8-0.85	41
0.85-0.9	6
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9364	High Similarity	NPC143533
0.875	High Similarity	NPC57994
0.875	High Similarity	NPC289299
0.8564	High Similarity	NPC258480
0.8564	High Similarity	NPC472119
0.847	Intermediate Similarity	NPC478077
0.847	Intermediate Similarity	NPC66210
0.8424	Intermediate Similarity	NPC472323
0.8415	Intermediate Similarity	NPC472107
0.8415	Intermediate Similarity	NPC79062
0.8404	Intermediate Similarity	NPC245916
0.8398	Intermediate Similarity	NPC15840
0.8298	Intermediate Similarity	NPC472295
0.8298	Intermediate Similarity	NPC472210
0.8298	Intermediate Similarity	NPC81802
0.8298	Intermediate Similarity	NPC247735
0.8298	Intermediate Similarity	NPC269886
0.8297	Intermediate Similarity	NPC469896
0.8289	Intermediate Similarity	NPC472097
0.8287	Intermediate Similarity	NPC234987
0.8207	Intermediate Similarity	NPC472104
0.8182	Intermediate Similarity	NPC102338
0.8182	Intermediate Similarity	NPC196251
0.8182	Intermediate Similarity	NPC63199
0.8182	Intermediate Similarity	NPC111602
0.8138	Intermediate Similarity	NPC472112
0.8125	Intermediate Similarity	NPC52557
0.8085	Intermediate Similarity	NPC175474
0.8079	Intermediate Similarity	NPC81229
0.8079	Intermediate Similarity	NPC255229
0.8054	Intermediate Similarity	NPC113626
0.8053	Intermediate Similarity	NPC472113
0.8034	Intermediate Similarity	NPC194881
0.8011	Intermediate Similarity	NPC159125
0.7969	Intermediate Similarity	NPC220151
0.7969	Intermediate Similarity	NPC19692
0.7958	Intermediate Similarity	NPC472292
0.7949	Intermediate Similarity	NPC128265
0.7949	Intermediate Similarity	NPC199851
0.7949	Intermediate Similarity	NPC294909
0.7949	Intermediate Similarity	NPC254240
0.7949	Intermediate Similarity	NPC312870
0.7946	Intermediate Similarity	NPC219336
0.7927	Intermediate Similarity	NPC472293
0.7921	Intermediate Similarity	NPC472291
0.7892	Intermediate Similarity	NPC217372
0.7892	Intermediate Similarity	NPC183662
0.7892	Intermediate Similarity	NPC15573
0.7889	Intermediate Similarity	NPC271797
0.7889	Intermediate Similarity	NPC21174
0.7887	Intermediate Similarity	NPC469736
0.7879	Intermediate Similarity	NPC132539
0.7857	Intermediate Similarity	NPC49196
0.7857	Intermediate Similarity	NPC79129
0.7857	Intermediate Similarity	NPC195461
0.7857	Intermediate Similarity	NPC81654
0.7857	Intermediate Similarity	NPC249150
0.7857	Intermediate Similarity	NPC313985
0.7849	Intermediate Similarity	NPC133261
0.7839	Intermediate Similarity	NPC238457
0.7838	Intermediate Similarity	NPC24594
0.7838	Intermediate Similarity	NPC472122
0.7807	Intermediate Similarity	NPC472105
0.7807	Intermediate Similarity	NPC187827
0.7806	Intermediate Similarity	NPC472296
0.7806	Intermediate Similarity	NPC472297
0.7778	Intermediate Similarity	NPC57398
0.7755	Intermediate Similarity	NPC50503
0.7716	Intermediate Similarity	NPC81535
0.7684	Intermediate Similarity	NPC46895
0.7668	Intermediate Similarity	NPC329858
0.7668	Intermediate Similarity	NPC314333
0.7653	Intermediate Similarity	NPC79356
0.7653	Intermediate Similarity	NPC102592
0.7644	Intermediate Similarity	NPC133003
0.7632	Intermediate Similarity	NPC472109
0.7632	Intermediate Similarity	NPC472110
0.7629	Intermediate Similarity	NPC473763
0.7629	Intermediate Similarity	NPC117244
0.7619	Intermediate Similarity	NPC73994
0.7619	Intermediate Similarity	NPC61011
0.7612	Intermediate Similarity	NPC327592
0.761	Intermediate Similarity	NPC318299
0.761	Intermediate Similarity	NPC472098
0.7608	Intermediate Similarity	NPC472099
0.7606	Intermediate Similarity	NPC326575
0.7606	Intermediate Similarity	NPC145885
0.7606	Intermediate Similarity	NPC14113
0.7606	Intermediate Similarity	NPC84827
0.7577	Intermediate Similarity	NPC324091
0.7574	Intermediate Similarity	NPC317373
0.7573	Intermediate Similarity	NPC221100
0.7573	Intermediate Similarity	NPC234078
0.7573	Intermediate Similarity	NPC317752
0.7553	Intermediate Similarity	NPC84347
0.754	Intermediate Similarity	NPC161861
0.754	Intermediate Similarity	NPC472123
0.7538	Intermediate Similarity	NPC123395
0.7524	Intermediate Similarity	NPC118940
0.7524	Intermediate Similarity	NPC264176
0.7513	Intermediate Similarity	NPC83774
0.7512	Intermediate Similarity	NPC143977
0.7512	Intermediate Similarity	NPC328318
0.7512	Intermediate Similarity	NPC328596
0.75	Intermediate Similarity	NPC229893
0.75	Intermediate Similarity	NPC121327
0.75	Intermediate Similarity	NPC469938
0.75	Intermediate Similarity	NPC266249
0.7488	Intermediate Similarity	NPC472065
0.7487	Intermediate Similarity	NPC474916
0.7477	Intermediate Similarity	NPC478078
0.7475	Intermediate Similarity	NPC128244
0.746	Intermediate Similarity	NPC151635
0.7452	Intermediate Similarity	NPC477979
0.7448	Intermediate Similarity	NPC139291
0.7448	Intermediate Similarity	NPC472108
0.7438	Intermediate Similarity	NPC314648
0.7437	Intermediate Similarity	NPC141454
0.7427	Intermediate Similarity	NPC123839
0.7426	Intermediate Similarity	NPC162730
0.7423	Intermediate Similarity	NPC141612
0.7423	Intermediate Similarity	NPC17273
0.7423	Intermediate Similarity	NPC135601
0.7421	Intermediate Similarity	NPC157583
0.7419	Intermediate Similarity	NPC472115
0.7419	Intermediate Similarity	NPC472114
0.7413	Intermediate Similarity	NPC214428
0.7411	Intermediate Similarity	NPC55493
0.7403	Intermediate Similarity	NPC281094
0.7402	Intermediate Similarity	NPC314855
0.7402	Intermediate Similarity	NPC313345
0.7402	Intermediate Similarity	NPC315638
0.7402	Intermediate Similarity	NPC313796
0.7402	Intermediate Similarity	NPC472064
0.7396	Intermediate Similarity	NPC191415
0.7393	Intermediate Similarity	NPC52254
0.7389	Intermediate Similarity	NPC165599
0.7385	Intermediate Similarity	NPC329631
0.7382	Intermediate Similarity	NPC248041
0.7382	Intermediate Similarity	NPC126709
0.7382	Intermediate Similarity	NPC248462
0.7376	Intermediate Similarity	NPC471944
0.7371	Intermediate Similarity	NPC282103
0.7366	Intermediate Similarity	NPC314297
0.7366	Intermediate Similarity	NPC53344
0.7366	Intermediate Similarity	NPC315545
0.7366	Intermediate Similarity	NPC115232
0.7361	Intermediate Similarity	NPC33949
0.7354	Intermediate Similarity	NPC252572
0.7346	Intermediate Similarity	NPC281049
0.7344	Intermediate Similarity	NPC91179
0.734	Intermediate Similarity	NPC472062
0.734	Intermediate Similarity	NPC474116
0.734	Intermediate Similarity	NPC472069
0.734	Intermediate Similarity	NPC472063
0.7337	Intermediate Similarity	NPC202812
0.7336	Intermediate Similarity	NPC475271
0.7333	Intermediate Similarity	NPC62749
0.7333	Intermediate Similarity	NPC152768
0.7333	Intermediate Similarity	NPC148183
0.7333	Intermediate Similarity	NPC235684
0.733	Intermediate Similarity	NPC28848
0.733	Intermediate Similarity	NPC14325
0.7326	Intermediate Similarity	NPC56233
0.7326	Intermediate Similarity	NPC114637
0.732	Intermediate Similarity	NPC477003
0.7317	Intermediate Similarity	NPC277350
0.7316	Intermediate Similarity	NPC469529
0.7313	Intermediate Similarity	NPC149708
0.7312	Intermediate Similarity	NPC469541
0.731	Intermediate Similarity	NPC469501
0.731	Intermediate Similarity	NPC469470
0.7308	Intermediate Similarity	NPC478076
0.7299	Intermediate Similarity	NPC312645
0.7295	Intermediate Similarity	NPC472070
0.7292	Intermediate Similarity	NPC283219
0.7287	Intermediate Similarity	NPC317430
0.7286	Intermediate Similarity	NPC267343
0.7282	Intermediate Similarity	NPC477065
0.7277	Intermediate Similarity	NPC267885
0.7264	Intermediate Similarity	NPC167710
0.7264	Intermediate Similarity	NPC106824
0.7263	Intermediate Similarity	NPC191310
0.726	Intermediate Similarity	NPC314834
0.7259	Intermediate Similarity	NPC221873
0.7258	Intermediate Similarity	NPC242116
0.7251	Intermediate Similarity	NPC36405
0.7249	Intermediate Similarity	NPC65080
0.7247	Intermediate Similarity	NPC20144
0.7245	Intermediate Similarity	NPC118084
0.7238	Intermediate Similarity	NPC89508
0.7236	Intermediate Similarity	NPC216550
0.7233	Intermediate Similarity	NPC471191
0.7225	Intermediate Similarity	NPC203468
0.7225	Intermediate Similarity	NPC149155
0.7225	Intermediate Similarity	NPC110500
0.7222	Intermediate Similarity	NPC154339
0.722	Intermediate Similarity	NPC476098
0.722	Intermediate Similarity	NPC317701
0.7219	Intermediate Similarity	NPC265100

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 NPC472116 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	512
0.2-0.3	727
0.3-0.4	1732
0.4-0.5	2424
0.5-0.6	2439
0.6-0.7	965
0.7-0.8	151
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD4602	Approved
0.8316	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.8173	Intermediate Similarity	NPD4520	Approved
0.7949	Intermediate Similarity	NPD4500	Approved
0.7949	Intermediate Similarity	NPD4501	Approved
0.7944	Intermediate Similarity	NPD2915	Discontinued
0.7935	Intermediate Similarity	NPD5104	Approved
0.7931	Intermediate Similarity	NPD3389	Approved
0.7931	Intermediate Similarity	NPD3393	Approved
0.7931	Intermediate Similarity	NPD3394	Approved
0.7857	Intermediate Similarity	NPD4601	Approved
0.7857	Intermediate Similarity	NPD4600	Approved
0.7806	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD1630	Approved
0.77	Intermediate Similarity	NPD6987	Phase 1
0.7688	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD4499	Approved
0.7665	Intermediate Similarity	NPD4397	Phase 1
0.7644	Intermediate Similarity	NPD5075	Discontinued
0.7629	Intermediate Similarity	NPD2336	Approved
0.7622	Intermediate Similarity	NPD1575	Approved
0.7622	Intermediate Similarity	NPD1573	Approved
0.7604	Intermediate Similarity	NPD5809	Phase 3
0.76	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD1631	Approved
0.7562	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD750	Phase 2
0.75	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7665	Phase 2
0.75	Intermediate Similarity	NPD7666	Phase 3
0.7475	Intermediate Similarity	NPD2307	Discontinued
0.7474	Intermediate Similarity	NPD4948	Discontinued
0.7473	Intermediate Similarity	NPD4326	Phase 2
0.7447	Intermediate Similarity	NPD4524	Discontinued
0.744	Intermediate Similarity	NPD7455	Approved
0.744	Intermediate Similarity	NPD7454	Approved
0.7438	Intermediate Similarity	NPD3947	Discontinued
0.7415	Intermediate Similarity	NPD2509	Approved
0.7415	Intermediate Similarity	NPD2510	Approved
0.7409	Intermediate Similarity	NPD7482	Phase 2
0.7409	Intermediate Similarity	NPD7483	Phase 2
0.7402	Intermediate Similarity	NPD7568	Phase 1
0.7397	Intermediate Similarity	NPD5891	Approved
0.7396	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7393	Intermediate Similarity	NPD6770	Approved
0.7387	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD6999	Discontinued
0.7353	Intermediate Similarity	NPD8114	Approved
0.7353	Intermediate Similarity	NPD8115	Approved
0.7344	Intermediate Similarity	NPD5473	Discontinued
0.7337	Intermediate Similarity	NPD2213	Approved
0.7337	Intermediate Similarity	NPD2214	Approved
0.7326	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7001	Phase 3
0.7316	Intermediate Similarity	NPD1586	Approved
0.7299	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7944	Discontinued
0.7238	Intermediate Similarity	NPD6787	Phase 2
0.7235	Intermediate Similarity	NPD7994	Phase 2
0.7235	Intermediate Similarity	NPD3259	Approved
0.7234	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD2091	Phase 2
0.7231	Intermediate Similarity	NPD2096	Phase 2
0.7225	Intermediate Similarity	NPD482	Approved
0.7225	Intermediate Similarity	NPD5475	Discontinued
0.7215	Intermediate Similarity	NPD7688	Phase 1
0.7214	Intermediate Similarity	NPD4848	Phase 1
0.7204	Intermediate Similarity	NPD5293	Phase 2
0.7202	Intermediate Similarity	NPD1587	Approved
0.7198	Intermediate Similarity	NPD3905	Phase 3
0.719	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6578	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2095	Phase 2
0.7179	Intermediate Similarity	NPD2094	Phase 2
0.7179	Intermediate Similarity	NPD2092	Phase 2
0.7177	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4952	Phase 3
0.7165	Intermediate Similarity	NPD6452	Discontinued
0.715	Intermediate Similarity	NPD7404	Approved
0.7129	Intermediate Similarity	NPD4506	Discontinued
0.7129	Intermediate Similarity	NPD7061	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD7817	Phase 1
0.7122	Intermediate Similarity	NPD7727	Phase 2
0.7122	Intermediate Similarity	NPD5017	Discontinued
0.7121	Intermediate Similarity	NPD4988	Discontinued
0.711	Intermediate Similarity	NPD5887	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7878	Phase 2
0.7101	Intermediate Similarity	NPD5901	Discontinued
0.71	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5003	Discontinued
0.7092	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD2879	Approved
0.7087	Intermediate Similarity	NPD2881	Approved
0.7085	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD4334	Discontinued
0.7079	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD5897	Approved
0.7077	Intermediate Similarity	NPD5899	Approved
0.7077	Intermediate Similarity	NPD5898	Approved
0.7075	Intermediate Similarity	NPD7557	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD4373	Phase 2
0.7071	Intermediate Similarity	NPD5444	Phase 1
0.7065	Intermediate Similarity	NPD5505	Discontinued
0.7056	Intermediate Similarity	NPD3805	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6178	Phase 3
0.7053	Intermediate Similarity	NPD6176	Phase 1
0.7041	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6790	Phase 1
0.703	Intermediate Similarity	NPD4348	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD3077	Approved
0.7026	Intermediate Similarity	NPD3079	Approved
0.7026	Intermediate Similarity	NPD3078	Approved
0.7026	Intermediate Similarity	NPD3076	Approved
0.7024	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7103	Approved
0.7018	Intermediate Similarity	NPD6173	Approved
0.7016	Intermediate Similarity	NPD1343	Approved
0.7015	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1658	Discontinued
0.701	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4385	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7232	Discontinued
0.7	Intermediate Similarity	NPD7234	Approved
0.7	Intermediate Similarity	NPD4882	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6292	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7233	Approved
0.7	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD1270	Approved
0.6991	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.699	Remote Similarity	NPD2481	Approved
0.699	Remote Similarity	NPD2479	Phase 3
0.6989	Remote Similarity	NPD3385	Approved
0.6986	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD3315	Phase 3
0.6983	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.697	Remote Similarity	NPD721	Approved
0.697	Remote Similarity	NPD7564	Discontinued
0.6963	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1996	Discontinued
0.6955	Remote Similarity	NPD8289	Discontinued
0.6953	Remote Similarity	NPD8463	Approved
0.6943	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7308	Discontinued
0.6938	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD5426	Phase 3
0.6937	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4051	Discontinued
0.6931	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7730	Approved
0.6923	Remote Similarity	NPD7731	Approved
0.692	Remote Similarity	NPD7950	Approved
0.692	Remote Similarity	NPD7952	Approved
0.692	Remote Similarity	NPD7953	Approved
0.692	Remote Similarity	NPD7951	Approved
0.692	Remote Similarity	NPD7791	Approved
0.692	Remote Similarity	NPD7790	Approved
0.692	Remote Similarity	NPD7789	Approved
0.6919	Remote Similarity	NPD6487	Approved
0.6919	Remote Similarity	NPD6486	Approved
0.6912	Remote Similarity	NPD4427	Phase 2
0.6911	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7271	Approved
0.6908	Remote Similarity	NPD6479	Discontinued
0.6906	Remote Similarity	NPD5020	Approved
0.6905	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7470	Discontinued
0.69	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6665	Discontinued
0.6897	Remote Similarity	NPD4315	Phase 2
0.6895	Remote Similarity	NPD8356	Approved
0.6893	Remote Similarity	NPD7778	Approved
0.6893	Remote Similarity	NPD7777	Approved
0.6893	Remote Similarity	NPD53	Approved
0.6888	Remote Similarity	NPD7869	Discontinued
0.6881	Remote Similarity	NPD2564	Approved
0.6881	Remote Similarity	NPD2565	Phase 2
0.6869	Remote Similarity	NPD5866	Approved
0.6861	Remote Similarity	NPD7824	Approved
0.686	Remote Similarity	NPD6249	Phase 2
0.686	Remote Similarity	NPD6248	Phase 2
0.6856	Remote Similarity	NPD6716	Phase 1

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