NPASS Compound

Structure

NPC90967 OpenBabel07101719242D 27 32 0 0 1 0 0 0 0 0999 V2000 3.9716 -0.9956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8090 0.7338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2557 -1.6402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0673 -0.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0673 0.7794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2330 -0.6657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2330 1.2611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1943 -0.5582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9162 -1.2611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0992 -1.2803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -1.5567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4233 -1.0448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3987 -0.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2995 -0.6638 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3987 0.7794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2332 -0.4143 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3735 -0.8770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4436 -0.6256 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4825 -0.4817 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9162 0.2977 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4825 1.0771 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7751 -1.0448 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1.0081 -2.2364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6208 -1.8081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0562 -0.1973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 26 1 0 0 0 0 3 12 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 13 2 0 0 0 0 7 15 2 0 0 0 0 8 14 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 19 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 19 1 6 0 0 0 15 22 1 0 0 0 0 16 21 1 6 0 0 0 16 23 1 0 0 0 0 17 23 1 1 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 18 25 2 0 0 0 0 18 26 1 0 0 0 0 19 20 1 1 0 0 0 20 21 1 1 0 0 0 21 22 1 1 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.17
Volume:	364.406
LogP:	2.145
LogD:	2.193
LogS:	-3.813
# Rotatable Bonds:	3
TPSA:	71.03
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.611
Synthetic Accessibility Score:	6.457
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.531
MDCK Permeability:	2.0216080883983523e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.392
Human Intestinal Absorption (HIA):	0.58
20% Bioavailability (F20%):	0.08
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.887
Plasma Protein Binding (PPB):	71.960205078125%
Volume Distribution (VD):	1.406
Pgp-substrate:	26.45171356201172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.285
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.854
CYP2C9-inhibitor:	0.078
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.476
CYP3A4-inhibitor:	0.39
CYP3A4-substrate:	0.88

ADMET: Excretion

Clearance (CL):	11.446
Half-life (T1/2):	0.367

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.89
Drug-inuced Liver Injury (DILI):	0.49
AMES Toxicity:	0.919
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.648
Carcinogencity:	0.973
Eye Corrosion:	0.004
Eye Irritation:	0.019
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC90967

Natural Product ID:	NPC90967
*Common Name:**	MPNPJQYCBQXPGW-GGZNVOGHSA-N
IUPAC Name:	n.a.
Synonyms:	O-Deacetylpicraline
Standard InCHIKey:	MPNPJQYCBQXPGW-GGZNVOGHSA-N
Standard InCHI:	InChI=1S/C21H24N2O4/c1-3-12-10-23-16-8-14(12)19(11-24,18(25)26-2)20-9-17(23)27-21(16,20)22-15-7-5-4-6-13(15)20/h3-7,14,16-17,22,24H,8-11H2,1-2H3/b12-3-/t14-,16-,17-,19-,20-,21-/m0/s1
SMILES:	COC(=O)[C@]1(CO)[C@H]2C[C@H]3[C@@]45[C@@]1(C[C@H](O4)N3C/C/2=C/C)c1ccccc1N5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL589297
PubChem CID:	46229106
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002750] Corynanthean-type 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
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191551]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	leaves	Purwodadi Botanical Garden, Indonesia	n.a.	PMID[20189404]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[22148233]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	Barks	n.a.	n.a.	PMID[23806072]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19678	Alstonia macrophylla	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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT640	Individual Protein	Sodium/glucose cotransporter 1	Homo sapiens	Inhibition	=	10.1	%	PMID[519974]
NPT641	Individual Protein	Sodium/glucose cotransporter 2	Homo sapiens	Inhibition	=	-0.2	%	PMID[519974]

☑ 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 NPC90967 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	244
0.1-0.2	1237
0.2-0.3	3120
0.3-0.4	13479
0.4-0.5	19259
0.5-0.6	4423
0.6-0.7	786
0.7-0.8	141
0.8-0.85	3
0.85-0.9	1
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9548	High Similarity	NPC34717
0.954	High Similarity	NPC181928
0.9213	High Similarity	NPC473298
0.8622	High Similarity	NPC234772
0.8172	Intermediate Similarity	NPC52262
0.8019	Intermediate Similarity	NPC154922
0.8019	Intermediate Similarity	NPC231924
0.8	Intermediate Similarity	NPC475489
0.7959	Intermediate Similarity	NPC471512
0.7958	Intermediate Similarity	NPC25401
0.7835	Intermediate Similarity	NPC221687
0.7834	Intermediate Similarity	NPC113455
0.7727	Intermediate Similarity	NPC120239
0.7713	Intermediate Similarity	NPC218594
0.7713	Intermediate Similarity	NPC99043
0.7708	Intermediate Similarity	NPC14994
0.7704	Intermediate Similarity	NPC473375
0.7704	Intermediate Similarity	NPC97100
0.7692	Intermediate Similarity	NPC282339
0.7692	Intermediate Similarity	NPC99632
0.7684	Intermediate Similarity	NPC159963
0.7639	Intermediate Similarity	NPC476220
0.7639	Intermediate Similarity	NPC160113
0.7629	Intermediate Similarity	NPC22689
0.7629	Intermediate Similarity	NPC105055
0.7606	Intermediate Similarity	NPC203202
0.7606	Intermediate Similarity	NPC476441
0.7606	Intermediate Similarity	NPC264482
0.7592	Intermediate Similarity	NPC477159
0.7552	Intermediate Similarity	NPC97584
0.75	Intermediate Similarity	NPC476258
0.75	Intermediate Similarity	NPC476425
0.75	Intermediate Similarity	NPC304837
0.7486	Intermediate Similarity	NPC36495
0.7474	Intermediate Similarity	NPC186669
0.7446	Intermediate Similarity	NPC225319
0.7446	Intermediate Similarity	NPC248117
0.7435	Intermediate Similarity	NPC6974
0.7391	Intermediate Similarity	NPC193410
0.7391	Intermediate Similarity	NPC234999
0.7389	Intermediate Similarity	NPC1464
0.7366	Intermediate Similarity	NPC246140
0.7366	Intermediate Similarity	NPC195787
0.7358	Intermediate Similarity	NPC476428
0.7351	Intermediate Similarity	NPC474058
0.7351	Intermediate Similarity	NPC472102
0.7351	Intermediate Similarity	NPC309531
0.734	Intermediate Similarity	NPC224970
0.734	Intermediate Similarity	NPC223595
0.734	Intermediate Similarity	NPC167724
0.7337	Intermediate Similarity	NPC61013
0.7326	Intermediate Similarity	NPC472106
0.7321	Intermediate Similarity	NPC475778
0.7318	Intermediate Similarity	NPC264589
0.7312	Intermediate Similarity	NPC85651
0.7312	Intermediate Similarity	NPC472101
0.7312	Intermediate Similarity	NPC472120
0.7312	Intermediate Similarity	NPC286871
0.731	Intermediate Similarity	NPC284706
0.7297	Intermediate Similarity	NPC301501
0.7287	Intermediate Similarity	NPC472115
0.7287	Intermediate Similarity	NPC472114
0.7281	Intermediate Similarity	NPC473458
0.7258	Intermediate Similarity	NPC201424
0.7243	Intermediate Similarity	NPC113946
0.7225	Intermediate Similarity	NPC285622
0.7219	Intermediate Similarity	NPC176983
0.7212	Intermediate Similarity	NPC329932
0.7206	Intermediate Similarity	NPC79129
0.7206	Intermediate Similarity	NPC195461
0.7206	Intermediate Similarity	NPC313985
0.7206	Intermediate Similarity	NPC81654
0.7206	Intermediate Similarity	NPC49196
0.7206	Intermediate Similarity	NPC249150
0.7202	Intermediate Similarity	NPC471513
0.7202	Intermediate Similarity	NPC476326
0.72	Intermediate Similarity	NPC469452
0.7196	Intermediate Similarity	NPC288110
0.7196	Intermediate Similarity	NPC214960
0.7196	Intermediate Similarity	NPC279527
0.7192	Intermediate Similarity	NPC138615
0.7192	Intermediate Similarity	NPC132874
0.7192	Intermediate Similarity	NPC218733
0.7192	Intermediate Similarity	NPC265642
0.7172	Intermediate Similarity	NPC21425
0.7165	Intermediate Similarity	NPC321211
0.7151	Intermediate Similarity	NPC123241
0.7135	Intermediate Similarity	NPC214626
0.7135	Intermediate Similarity	NPC21752
0.7135	Intermediate Similarity	NPC139085
0.7135	Intermediate Similarity	NPC298851
0.7135	Intermediate Similarity	NPC276993
0.7135	Intermediate Similarity	NPC181138
0.7135	Intermediate Similarity	NPC210415
0.7135	Intermediate Similarity	NPC293255
0.7135	Intermediate Similarity	NPC251212
0.7128	Intermediate Similarity	NPC472121
0.7128	Intermediate Similarity	NPC293458
0.7124	Intermediate Similarity	NPC469451
0.712	Intermediate Similarity	NPC472118
0.7111	Intermediate Similarity	NPC469450
0.711	Intermediate Similarity	NPC477394
0.7108	Intermediate Similarity	NPC50503
0.71	Intermediate Similarity	NPC5630
0.71	Intermediate Similarity	NPC474059
0.7098	Intermediate Similarity	NPC131977
0.7098	Intermediate Similarity	NPC469726
0.7098	Intermediate Similarity	NPC329338
0.7097	Intermediate Similarity	NPC29285
0.7081	Intermediate Similarity	NPC478076
0.7075	Intermediate Similarity	NPC127996
0.7072	Intermediate Similarity	NPC139373
0.707	Intermediate Similarity	NPC77777
0.7067	Intermediate Similarity	NPC477180
0.7067	Intermediate Similarity	NPC254850
0.7067	Intermediate Similarity	NPC477181
0.7067	Intermediate Similarity	NPC87714
0.7067	Intermediate Similarity	NPC477178
0.7065	Intermediate Similarity	NPC475763
0.7059	Intermediate Similarity	NPC302548
0.7059	Intermediate Similarity	NPC153694
0.7059	Intermediate Similarity	NPC211525
0.7059	Intermediate Similarity	NPC475559
0.7048	Intermediate Similarity	NPC471950
0.7048	Intermediate Similarity	NPC471945
0.7043	Intermediate Similarity	NPC473297
0.7041	Intermediate Similarity	NPC11149
0.7037	Intermediate Similarity	NPC472117
0.7035	Intermediate Similarity	NPC282092
0.7033	Intermediate Similarity	NPC477173
0.7033	Intermediate Similarity	NPC470490
0.7033	Intermediate Similarity	NPC477174
0.7021	Intermediate Similarity	NPC310403
0.7021	Intermediate Similarity	NPC97380
0.7021	Intermediate Similarity	NPC243673
0.7021	Intermediate Similarity	NPC63210
0.7021	Intermediate Similarity	NPC148468
0.7021	Intermediate Similarity	NPC263709
0.7019	Intermediate Similarity	NPC477179
0.7014	Intermediate Similarity	NPC471951
0.7014	Intermediate Similarity	NPC469743
0.7014	Intermediate Similarity	NPC471946
0.7005	Intermediate Similarity	NPC232600
0.7	Intermediate Similarity	NPC470488
0.6985	Remote Similarity	NPC322621
0.6982	Remote Similarity	NPC477397
0.6982	Remote Similarity	NPC223242
0.698	Remote Similarity	NPC203628
0.6974	Remote Similarity	NPC129624
0.6971	Remote Similarity	NPC471436
0.6971	Remote Similarity	NPC162730
0.6967	Remote Similarity	NPC475259
0.6967	Remote Similarity	NPC470491
0.6963	Remote Similarity	NPC52059
0.6963	Remote Similarity	NPC470069
0.6959	Remote Similarity	NPC96901
0.6959	Remote Similarity	NPC222046
0.6952	Remote Similarity	NPC277350
0.6935	Remote Similarity	NPC245741
0.693	Remote Similarity	NPC189661
0.6927	Remote Similarity	NPC303214
0.6923	Remote Similarity	NPC13367
0.692	Remote Similarity	NPC473486
0.692	Remote Similarity	NPC475316
0.6919	Remote Similarity	NPC475962
0.6913	Remote Similarity	NPC477393
0.6912	Remote Similarity	NPC470485
0.6911	Remote Similarity	NPC313757
0.6904	Remote Similarity	NPC475094
0.6901	Remote Similarity	NPC475359
0.6901	Remote Similarity	NPC191817
0.69	Remote Similarity	NPC476095
0.69	Remote Similarity	NPC469722
0.6895	Remote Similarity	NPC128476
0.6895	Remote Similarity	NPC315368
0.689	Remote Similarity	NPC474116
0.6881	Remote Similarity	NPC175474
0.6878	Remote Similarity	NPC19175
0.6875	Remote Similarity	NPC473781
0.6875	Remote Similarity	NPC470631
0.6875	Remote Similarity	NPC214428
0.6875	Remote Similarity	NPC35390
0.6872	Remote Similarity	NPC177261
0.6866	Remote Similarity	NPC195636
0.6866	Remote Similarity	NPC473837
0.6862	Remote Similarity	NPC161827
0.686	Remote Similarity	NPC52557
0.6856	Remote Similarity	NPC469915
0.6854	Remote Similarity	NPC477160
0.6853	Remote Similarity	NPC477396
0.6853	Remote Similarity	NPC260075
0.6839	Remote Similarity	NPC278887
0.6837	Remote Similarity	NPC475097
0.6832	Remote Similarity	NPC285841
0.6826	Remote Similarity	NPC477395
0.6825	Remote Similarity	NPC470489
0.6816	Remote Similarity	NPC259626
0.6814	Remote Similarity	NPC470483
0.6804	Remote Similarity	NPC223590
0.6794	Remote Similarity	NPC138830

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 NPC90967 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	455
0.2-0.3	696
0.3-0.4	1735
0.4-0.5	3849
0.5-0.6	2045
0.6-0.7	207
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7206	Intermediate Similarity	NPD4600	Approved
0.7206	Intermediate Similarity	NPD4601	Approved
0.6895	Remote Similarity	NPD7600	Phase 2
0.6893	Remote Similarity	NPD5184	Approved
0.6893	Remote Similarity	NPD5182	Approved
0.6893	Remote Similarity	NPD5185	Approved
0.6865	Remote Similarity	NPD5941	Approved
0.6865	Remote Similarity	NPD5942	Approved
0.6842	Remote Similarity	NPD7599	Phase 2
0.6832	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4120	Approved
0.6809	Remote Similarity	NPD4121	Phase 3
0.68	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5742	Approved
0.6772	Remote Similarity	NPD5741	Approved
0.6772	Remote Similarity	NPD5743	Approved
0.6717	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.665	Remote Similarity	NPD5504	Discontinued
0.6615	Remote Similarity	NPD8630	Approved
0.6604	Remote Similarity	NPD6238	Discontinued
0.6595	Remote Similarity	NPD5024	Approved
0.6583	Remote Similarity	NPD5466	Approved
0.6576	Remote Similarity	NPD3625	Discontinued
0.6573	Remote Similarity	NPD2613	Approved
0.6571	Remote Similarity	NPD5003	Discontinued
0.6571	Remote Similarity	NPD3828	Approved
0.6562	Remote Similarity	NPD1663	Discontinued
0.6562	Remote Similarity	NPD7105	Phase 1
0.6557	Remote Similarity	NPD6805	Discontinued
0.6556	Remote Similarity	NPD4745	Approved
0.6556	Remote Similarity	NPD2574	Discontinued
0.6556	Remote Similarity	NPD3614	Approved
0.6556	Remote Similarity	NPD3616	Approved
0.6556	Remote Similarity	NPD2571	Approved
0.6556	Remote Similarity	NPD4746	Phase 3
0.6556	Remote Similarity	NPD3090	Approved
0.6556	Remote Similarity	NPD3087	Approved
0.6556	Remote Similarity	NPD3089	Approved
0.6556	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3088	Approved
0.6556	Remote Similarity	NPD2570	Approved
0.6556	Remote Similarity	NPD2573	Approved
0.6556	Remote Similarity	NPD3615	Approved
0.6556	Remote Similarity	NPD2566	Approved
0.6552	Remote Similarity	NPD7962	Phase 2
0.654	Remote Similarity	NPD5197	Approved
0.654	Remote Similarity	NPD5196	Approved
0.654	Remote Similarity	NPD5194	Approved
0.6538	Remote Similarity	NPD6073	Approved
0.6535	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6878	Phase 2
0.6535	Remote Similarity	NPD6879	Phase 2
0.6531	Remote Similarity	NPD5430	Discontinued
0.6531	Remote Similarity	NPD7036	Phase 3
0.6531	Remote Similarity	NPD7035	Approved
0.6503	Remote Similarity	NPD6294	Approved
0.6503	Remote Similarity	NPD6295	Approved
0.6502	Remote Similarity	NPD3471	Approved
0.6502	Remote Similarity	NPD3470	Approved
0.6498	Remote Similarity	NPD4082	Approved
0.6489	Remote Similarity	NPD6416	Phase 2
0.6486	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4686	Approved
0.6484	Remote Similarity	NPD4684	Phase 3
0.6484	Remote Similarity	NPD4685	Phase 3
0.6476	Remote Similarity	NPD4602	Approved
0.6473	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8281	Discontinued
0.6455	Remote Similarity	NPD1801	Approved
0.6455	Remote Similarity	NPD4494	Approved
0.6455	Remote Similarity	NPD4492	Approved
0.6455	Remote Similarity	NPD1802	Approved
0.6453	Remote Similarity	NPD4329	Approved
0.6453	Remote Similarity	NPD4330	Approved
0.6436	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD7940	Phase 3
0.6417	Remote Similarity	NPD2820	Phase 3
0.6411	Remote Similarity	NPD8240	Discontinued
0.6404	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD3790	Phase 2
0.6392	Remote Similarity	NPD6571	Approved
0.6392	Remote Similarity	NPD6570	Approved
0.6391	Remote Similarity	NPD7824	Approved
0.639	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD2037	Approved
0.6364	Remote Similarity	NPD8466	Approved
0.6364	Remote Similarity	NPD4499	Approved
0.6364	Remote Similarity	NPD8467	Approved
0.6364	Remote Similarity	NPD2564	Approved
0.6364	Remote Similarity	NPD2365	Approved
0.6364	Remote Similarity	NPD2565	Phase 2
0.6364	Remote Similarity	NPD8465	Approved
0.6359	Remote Similarity	NPD1294	Discontinued
0.6359	Remote Similarity	NPD5725	Approved
0.6355	Remote Similarity	NPD3792	Approved
0.6354	Remote Similarity	NPD7606	Phase 3
0.635	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7295	Approved
0.6337	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD4493	Discontinued
0.6333	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD6557	Phase 2
0.6327	Remote Similarity	NPD3437	Discontinued
0.6327	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6326	Remote Similarity	NPD4500	Approved
0.6326	Remote Similarity	NPD4501	Approved
0.632	Remote Similarity	NPD8364	Approved
0.632	Remote Similarity	NPD8363	Approved
0.6318	Remote Similarity	NPD2431	Approved
0.6318	Remote Similarity	NPD2432	Approved
0.6309	Remote Similarity	NPD7791	Approved
0.6309	Remote Similarity	NPD7953	Approved
0.6309	Remote Similarity	NPD7790	Approved
0.6309	Remote Similarity	NPD7789	Approved
0.6309	Remote Similarity	NPD7951	Approved
0.6309	Remote Similarity	NPD7950	Approved
0.6309	Remote Similarity	NPD6723	Discontinued
0.6309	Remote Similarity	NPD7952	Approved
0.6308	Remote Similarity	NPD4668	Phase 2
0.6304	Remote Similarity	NPD7731	Approved
0.6304	Remote Similarity	NPD7730	Approved
0.63	Remote Similarity	NPD2454	Approved
0.63	Remote Similarity	NPD2455	Approved
0.6298	Remote Similarity	NPD5263	Approved
0.6296	Remote Similarity	NPD7487	Discontinued
0.6288	Remote Similarity	NPD7271	Approved
0.6287	Remote Similarity	NPD5997	Discontinued
0.6287	Remote Similarity	NPD7854	Phase 2
0.6286	Remote Similarity	NPD5928	Phase 1
0.6286	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD5426	Phase 3
0.6279	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD4455	Discontinued
0.6275	Remote Similarity	NPD5498	Phase 2
0.6274	Remote Similarity	NPD5610	Approved
0.6273	Remote Similarity	NPD4022	Approved
0.6273	Remote Similarity	NPD7300	Phase 3
0.6273	Remote Similarity	NPD3472	Approved
0.6273	Remote Similarity	NPD7302	Phase 3
0.6271	Remote Similarity	NPD4217	Approved
0.6271	Remote Similarity	NPD2610	Approved
0.6271	Remote Similarity	NPD4215	Approved
0.6271	Remote Similarity	NPD2612	Approved
0.6271	Remote Similarity	NPD3132	Approved
0.6271	Remote Similarity	NPD4218	Approved
0.6271	Remote Similarity	NPD2609	Approved
0.6271	Remote Similarity	NPD3131	Approved
0.6271	Remote Similarity	NPD2611	Approved
0.6271	Remote Similarity	NPD4216	Approved
0.6271	Remote Similarity	NPD2608	Approved
0.627	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5982	Phase 2
0.6265	Remote Similarity	NPD8426	Approved
0.6265	Remote Similarity	NPD8460	Approved
0.6265	Remote Similarity	NPD8425	Approved
0.6265	Remote Similarity	NPD8459	Approved
0.6261	Remote Similarity	NPD1945	Phase 1
0.6261	Remote Similarity	NPD7470	Discontinued
0.625	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4682	Phase 2
0.6245	Remote Similarity	NPD3912	Discontinued
0.6244	Remote Similarity	NPD3782	Discontinued
0.6244	Remote Similarity	NPD5190	Phase 2
0.6243	Remote Similarity	NPD4175	Approved
0.6243	Remote Similarity	NPD4177	Approved
0.6239	Remote Similarity	NPD2920	Discontinued
0.6239	Remote Similarity	NPD7205	Discontinued
0.6239	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD8429	Approved
0.6235	Remote Similarity	NPD8427	Approved
0.6235	Remote Similarity	NPD8428	Approved
0.6234	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD6978	Phase 2
0.6233	Remote Similarity	NPD7301	Phase 3
0.6233	Remote Similarity	NPD3888	Discontinued
0.623	Remote Similarity	NPD5581	Approved
0.6227	Remote Similarity	NPD4596	Phase 1
0.6226	Remote Similarity	NPD7570	Approved
0.6226	Remote Similarity	NPD7569	Approved
0.6218	Remote Similarity	NPD5748	Phase 2
0.6216	Remote Similarity	NPD5860	Discontinued
0.6216	Remote Similarity	NPD3372	Discontinued
0.6212	Remote Similarity	NPD2506	Approved
0.6207	Remote Similarity	NPD7780	Approved
0.6207	Remote Similarity	NPD7781	Approved
0.6205	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD5086	Approved
0.6204	Remote Similarity	NPD6874	Approved
0.6204	Remote Similarity	NPD5608	Approved
0.6204	Remote Similarity	NPD5609	Approved
0.6198	Remote Similarity	NPD7478	Approved
0.6196	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4603	Phase 2
0.6195	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6192	Remote Similarity	NPD7770	Phase 3
0.6186	Remote Similarity	NPD5195	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data