NPASS Compound

Structure

NPC34717 OpenBabel07101718192D 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 2 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:	366.16
Volume:	361.769
LogP:	1.969
LogD:	2.138
LogS:	-3.97
# Rotatable Bonds:	3
TPSA:	67.87
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.373
Synthetic Accessibility Score:	6.517
Fsp3:	0.524
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.315
MDCK Permeability:	2.23509796342114e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.254
Human Intestinal Absorption (HIA):	0.586
20% Bioavailability (F20%):	0.311
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.928
Plasma Protein Binding (PPB):	68.22686004638672%
Volume Distribution (VD):	1.676
Pgp-substrate:	38.62141418457031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.335
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.791
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.233
CYP3A4-inhibitor:	0.723
CYP3A4-substrate:	0.893

ADMET: Excretion

Clearance (CL):	11.375
Half-life (T1/2):	0.222

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.853
Drug-inuced Liver Injury (DILI):	0.612
AMES Toxicity:	0.98
Rat Oral Acute Toxicity:	0.976
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.925
Carcinogencity:	0.961
Eye Corrosion:	0.005
Eye Irritation:	0.024
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC34717

Natural Product ID:	NPC34717
*Common Name:**	Picralinal
IUPAC Name:	n.a.
Synonyms:	Picralinal
Standard InCHIKey:	RHBAENOZUZWALZ-GGZNVOGHSA-N
Standard InCHI:	InChI=1S/C21H22N2O4/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/h3-7,11,14,16-17,22H,8-10H2,1-2H3/b12-3-/t14-,16-,17-,19-,20-,21-/m0/s1
SMILES:	C/C=C1/CN2[C@H]3C[C@@H]1[C@@](C=O)(C(=O)OC)[C@]14C[C@@H]2O[C@@]34Nc2ccccc12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL590273
PubChem CID:	46229103
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	=	16.5	%	PMID[466341]
NPT641	Individual Protein	Sodium/glucose cotransporter 2	Homo sapiens	Inhibition	=	36.3	%	PMID[466341]

☑ 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 NPC34717 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	289
0.1-0.2	1504
0.2-0.3	4079
0.3-0.4	18911
0.4-0.5	13714
0.5-0.6	3503
0.6-0.7	602
0.7-0.8	88
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9651	High Similarity	NPC181928
0.9548	High Similarity	NPC90967
0.9429	High Similarity	NPC473298
0.8241	Intermediate Similarity	NPC234772
0.8098	Intermediate Similarity	NPC231924
0.8042	Intermediate Similarity	NPC25401
0.8009	Intermediate Similarity	NPC154922
0.7824	Intermediate Similarity	NPC113455
0.7789	Intermediate Similarity	NPC14994
0.7778	Intermediate Similarity	NPC99632
0.7778	Intermediate Similarity	NPC282339
0.7778	Intermediate Similarity	NPC52262
0.7766	Intermediate Similarity	NPC159963
0.7717	Intermediate Similarity	NPC120239
0.7716	Intermediate Similarity	NPC475489
0.7688	Intermediate Similarity	NPC264482
0.7688	Intermediate Similarity	NPC203202
0.7628	Intermediate Similarity	NPC476220
0.7628	Intermediate Similarity	NPC160113
0.7588	Intermediate Similarity	NPC471512
0.7553	Intermediate Similarity	NPC186669
0.7527	Intermediate Similarity	NPC248117
0.7527	Intermediate Similarity	NPC225319
0.7513	Intermediate Similarity	NPC6974
0.7489	Intermediate Similarity	NPC304837
0.7489	Intermediate Similarity	NPC476258
0.7487	Intermediate Similarity	NPC476425
0.7473	Intermediate Similarity	NPC193410
0.7462	Intermediate Similarity	NPC221687
0.7436	Intermediate Similarity	NPC105055
0.7436	Intermediate Similarity	NPC22689
0.7421	Intermediate Similarity	NPC218594
0.7421	Intermediate Similarity	NPC99043
0.7419	Intermediate Similarity	NPC167724
0.7419	Intermediate Similarity	NPC223595
0.7419	Intermediate Similarity	NPC224970
0.7418	Intermediate Similarity	NPC61013
0.7391	Intermediate Similarity	NPC286871
0.7337	Intermediate Similarity	NPC201424
0.7337	Intermediate Similarity	NPC97100
0.7337	Intermediate Similarity	NPC473375
0.7322	Intermediate Similarity	NPC113946
0.7302	Intermediate Similarity	NPC285622
0.7297	Intermediate Similarity	NPC176983
0.7283	Intermediate Similarity	NPC36495
0.7273	Intermediate Similarity	NPC279527
0.7273	Intermediate Similarity	NPC214960
0.7268	Intermediate Similarity	NPC97584
0.7245	Intermediate Similarity	NPC21425
0.724	Intermediate Similarity	NPC321211
0.7228	Intermediate Similarity	NPC123241
0.7225	Intermediate Similarity	NPC476441
0.7216	Intermediate Similarity	NPC477159
0.7211	Intermediate Similarity	NPC251212
0.7211	Intermediate Similarity	NPC214626
0.7211	Intermediate Similarity	NPC139085
0.7204	Intermediate Similarity	NPC293458
0.7188	Intermediate Similarity	NPC476326
0.7174	Intermediate Similarity	NPC29285
0.7173	Intermediate Similarity	NPC329338
0.7173	Intermediate Similarity	NPC469726
0.7158	Intermediate Similarity	NPC478076
0.7136	Intermediate Similarity	NPC77777
0.7136	Intermediate Similarity	NPC139373
0.7122	Intermediate Similarity	NPC1464
0.712	Intermediate Similarity	NPC473297
0.7101	Intermediate Similarity	NPC246140
0.7101	Intermediate Similarity	NPC195787
0.709	Intermediate Similarity	NPC472114
0.709	Intermediate Similarity	NPC472115
0.7085	Intermediate Similarity	NPC131977
0.7062	Intermediate Similarity	NPC475778
0.7059	Intermediate Similarity	NPC309531
0.7059	Intermediate Similarity	NPC472102
0.7059	Intermediate Similarity	NPC474058
0.7056	Intermediate Similarity	NPC322621
0.7048	Intermediate Similarity	NPC234999
0.7045	Intermediate Similarity	NPC223242
0.7035	Intermediate Similarity	NPC284706
0.7031	Intermediate Similarity	NPC96901
0.7021	Intermediate Similarity	NPC85651
0.7021	Intermediate Similarity	NPC472101
0.7021	Intermediate Similarity	NPC472120
0.7017	Intermediate Similarity	NPC264589
0.701	Intermediate Similarity	NPC132874
0.701	Intermediate Similarity	NPC138615
0.701	Intermediate Similarity	NPC265642
0.701	Intermediate Similarity	NPC218733
0.6995	Remote Similarity	NPC13367
0.699	Remote Similarity	NPC476428
0.6978	Remote Similarity	NPC301501
0.697	Remote Similarity	NPC476095
0.696	Remote Similarity	NPC469451
0.6957	Remote Similarity	NPC162730
0.6955	Remote Similarity	NPC473458
0.6947	Remote Similarity	NPC469450
0.6947	Remote Similarity	NPC472106
0.6943	Remote Similarity	NPC276993
0.6943	Remote Similarity	NPC293255
0.6943	Remote Similarity	NPC177261
0.6943	Remote Similarity	NPC21752
0.6943	Remote Similarity	NPC181138
0.6943	Remote Similarity	NPC210415
0.6943	Remote Similarity	NPC298851
0.6938	Remote Similarity	NPC277350
0.6935	Remote Similarity	NPC161827
0.6931	Remote Similarity	NPC472121
0.693	Remote Similarity	NPC195636
0.6923	Remote Similarity	NPC260075
0.6915	Remote Similarity	NPC5630
0.69	Remote Similarity	NPC285841
0.69	Remote Similarity	NPC329932
0.6886	Remote Similarity	NPC469452
0.6884	Remote Similarity	NPC259626
0.6878	Remote Similarity	NPC471513
0.6875	Remote Similarity	NPC474116
0.6866	Remote Similarity	NPC288110
0.6862	Remote Similarity	NPC153694
0.6862	Remote Similarity	NPC211525
0.686	Remote Similarity	NPC79129
0.686	Remote Similarity	NPC313985
0.686	Remote Similarity	NPC214428
0.686	Remote Similarity	NPC81654
0.686	Remote Similarity	NPC138830
0.686	Remote Similarity	NPC49196
0.686	Remote Similarity	NPC195461
0.686	Remote Similarity	NPC249150
0.6853	Remote Similarity	NPC11149
0.6839	Remote Similarity	NPC472118
0.6835	Remote Similarity	NPC476069
0.6834	Remote Similarity	NPC2933
0.6825	Remote Similarity	NPC310403
0.6825	Remote Similarity	NPC263709
0.6825	Remote Similarity	NPC97380
0.6825	Remote Similarity	NPC243673
0.6825	Remote Similarity	NPC63210
0.6825	Remote Similarity	NPC148468
0.6822	Remote Similarity	NPC127996
0.681	Remote Similarity	NPC477181
0.681	Remote Similarity	NPC87714
0.681	Remote Similarity	NPC477180
0.681	Remote Similarity	NPC477178
0.681	Remote Similarity	NPC254850
0.6798	Remote Similarity	NPC203628
0.6798	Remote Similarity	NPC22476
0.6796	Remote Similarity	NPC162440
0.6796	Remote Similarity	NPC302548
0.6796	Remote Similarity	NPC475559
0.6794	Remote Similarity	NPC471436
0.6792	Remote Similarity	NPC471945
0.6792	Remote Similarity	NPC471950
0.6787	Remote Similarity	NPC477394
0.6784	Remote Similarity	NPC256288
0.6779	Remote Similarity	NPC67904
0.6777	Remote Similarity	NPC477174
0.6777	Remote Similarity	NPC477173
0.6777	Remote Similarity	NPC470490
0.6774	Remote Similarity	NPC475763
0.6772	Remote Similarity	NPC222029
0.6771	Remote Similarity	NPC52059
0.6771	Remote Similarity	NPC470069
0.6766	Remote Similarity	NPC282092
0.6763	Remote Similarity	NPC50503
0.6763	Remote Similarity	NPC100863
0.6762	Remote Similarity	NPC477179
0.6761	Remote Similarity	NPC471951
0.6761	Remote Similarity	NPC469743
0.6761	Remote Similarity	NPC471946
0.6754	Remote Similarity	NPC472117
0.6754	Remote Similarity	NPC469741
0.675	Remote Similarity	NPC472119
0.6749	Remote Similarity	NPC474059
0.6748	Remote Similarity	NPC303214
0.6746	Remote Similarity	NPC232600
0.6745	Remote Similarity	NPC470488
0.6732	Remote Similarity	NPC470485
0.6729	Remote Similarity	NPC475359
0.6729	Remote Similarity	NPC191817
0.6727	Remote Similarity	NPC128476
0.6719	Remote Similarity	NPC313757
0.6716	Remote Similarity	NPC472209
0.6714	Remote Similarity	NPC470491
0.6714	Remote Similarity	NPC475259
0.6712	Remote Similarity	NPC19175
0.6702	Remote Similarity	NPC143457
0.67	Remote Similarity	NPC292675
0.6699	Remote Similarity	NPC243626
0.6683	Remote Similarity	NPC473615
0.6682	Remote Similarity	NPC189661
0.6667	Remote Similarity	NPC469915
0.6667	Remote Similarity	NPC477397
0.6667	Remote Similarity	NPC469722
0.6651	Remote Similarity	NPC475147
0.665	Remote Similarity	NPC229484
0.665	Remote Similarity	NPC475962
0.6649	Remote Similarity	NPC278887
0.6637	Remote Similarity	NPC470631
0.6637	Remote Similarity	NPC473781
0.6637	Remote Similarity	NPC35390
0.6636	Remote Similarity	NPC222046

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 NPC34717 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	524
0.2-0.3	740
0.3-0.4	1895
0.4-0.5	3961
0.5-0.6	1717
0.6-0.7	137
0.7-0.8	0
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
0.6971	Remote Similarity	NPD5185	Approved
0.6971	Remote Similarity	NPD5182	Approved
0.6971	Remote Similarity	NPD5184	Approved
0.686	Remote Similarity	NPD4600	Approved
0.686	Remote Similarity	NPD4601	Approved
0.6757	Remote Similarity	NPD5942	Approved
0.6757	Remote Similarity	NPD5941	Approved
0.6702	Remote Similarity	NPD7600	Phase 2
0.6667	Remote Similarity	NPD6238	Discontinued
0.665	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7599	Phase 2
0.6598	Remote Similarity	NPD7035	Approved
0.6598	Remote Similarity	NPD7036	Phase 3
0.6553	Remote Similarity	NPD5504	Discontinued
0.6535	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD8281	Discontinued
0.6533	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4120	Approved
0.6526	Remote Similarity	NPD4121	Phase 3
0.6524	Remote Similarity	NPD1801	Approved
0.6524	Remote Similarity	NPD1802	Approved
0.651	Remote Similarity	NPD8630	Approved
0.6492	Remote Similarity	NPD5742	Approved
0.6492	Remote Similarity	NPD5741	Approved
0.6492	Remote Similarity	NPD5743	Approved
0.6482	Remote Similarity	NPD7940	Phase 3
0.6476	Remote Similarity	NPD3828	Approved
0.6458	Remote Similarity	NPD6570	Approved
0.6458	Remote Similarity	NPD6571	Approved
0.6425	Remote Similarity	NPD4499	Approved
0.6425	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD4082	Approved
0.6404	Remote Similarity	NPD3471	Approved
0.6404	Remote Similarity	NPD3470	Approved
0.64	Remote Similarity	NPD5466	Approved
0.6398	Remote Similarity	NPD5024	Approved
0.6396	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD6805	Discontinued
0.6385	Remote Similarity	NPD4500	Approved
0.6385	Remote Similarity	NPD4501	Approved
0.6384	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD3625	Discontinued
0.6373	Remote Similarity	NPD7105	Phase 1
0.6373	Remote Similarity	NPD1663	Discontinued
0.6364	Remote Similarity	NPD7487	Discontinued
0.6364	Remote Similarity	NPD4492	Approved
0.6364	Remote Similarity	NPD4494	Approved
0.6355	Remote Similarity	NPD6878	Phase 2
0.6355	Remote Similarity	NPD4330	Approved
0.6355	Remote Similarity	NPD6879	Phase 2
0.6355	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD4329	Approved
0.635	Remote Similarity	NPD7854	Phase 2
0.635	Remote Similarity	NPD5997	Discontinued
0.6346	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD5430	Discontinued
0.6339	Remote Similarity	NPD6073	Approved
0.6338	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD7606	Phase 3
0.6321	Remote Similarity	NPD5003	Discontinued
0.6318	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD3437	Discontinued
0.6305	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6295	Approved
0.6304	Remote Similarity	NPD6294	Approved
0.6303	Remote Similarity	NPD4602	Approved
0.6296	Remote Similarity	NPD6416	Phase 2
0.6291	Remote Similarity	NPD5197	Approved
0.6291	Remote Similarity	NPD5196	Approved
0.6291	Remote Similarity	NPD5194	Approved
0.6281	Remote Similarity	NPD2037	Approved
0.6267	Remote Similarity	NPD1294	Discontinued
0.6264	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7478	Approved
0.6256	Remote Similarity	NPD3792	Approved
0.625	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD4493	Discontinued
0.6238	Remote Similarity	NPD8240	Discontinued
0.6234	Remote Similarity	NPD7824	Approved
0.6231	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7528	Approved
0.6228	Remote Similarity	NPD3912	Discontinued
0.6223	Remote Similarity	NPD2820	Phase 3
0.6219	Remote Similarity	NPD2432	Approved
0.6219	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD2431	Approved
0.6214	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7962	Phase 2
0.6212	Remote Similarity	NPD3790	Phase 2
0.6212	Remote Similarity	NPD8008	Approved
0.6212	Remote Similarity	NPD8007	Approved
0.6211	Remote Similarity	NPD4041	Approved
0.6207	Remote Similarity	NPD7688	Phase 1
0.6204	Remote Similarity	NPD6321	Discontinued
0.62	Remote Similarity	NPD2454	Approved
0.62	Remote Similarity	NPD2455	Approved
0.6195	Remote Similarity	NPD6770	Approved
0.6193	Remote Similarity	NPD7244	Discontinued
0.619	Remote Similarity	NPD5918	Discontinued
0.6188	Remote Similarity	NPD4455	Discontinued
0.6188	Remote Similarity	NPD2613	Approved
0.6183	Remote Similarity	NPD1109	Approved
0.6183	Remote Similarity	NPD1110	Approved
0.6182	Remote Similarity	NPD3472	Approved
0.6182	Remote Similarity	NPD4022	Approved
0.6176	Remote Similarity	NPD5600	Discontinued
0.6175	Remote Similarity	NPD2566	Approved
0.6175	Remote Similarity	NPD3090	Approved
0.6175	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD3089	Approved
0.6175	Remote Similarity	NPD3088	Approved
0.6175	Remote Similarity	NPD4746	Phase 3
0.6175	Remote Similarity	NPD2574	Discontinued
0.6175	Remote Similarity	NPD4745	Approved
0.6175	Remote Similarity	NPD3616	Approved
0.6175	Remote Similarity	NPD2571	Approved
0.6175	Remote Similarity	NPD3087	Approved
0.6175	Remote Similarity	NPD2570	Approved
0.6175	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD2573	Approved
0.6175	Remote Similarity	NPD3615	Approved
0.6175	Remote Similarity	NPD3614	Approved
0.6171	Remote Similarity	NPD1945	Phase 1
0.617	Remote Similarity	NPD2365	Approved
0.6167	Remote Similarity	NPD5993	Phase 1
0.6162	Remote Similarity	NPD5725	Approved
0.6161	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD5933	Phase 3
0.6158	Remote Similarity	NPD5932	Phase 3
0.6158	Remote Similarity	NPD5931	Phase 3
0.6157	Remote Similarity	NPD8466	Approved
0.6157	Remote Similarity	NPD8465	Approved
0.6157	Remote Similarity	NPD8467	Approved
0.6154	Remote Similarity	NPD7708	Approved
0.6154	Remote Similarity	NPD7952	Approved
0.6154	Remote Similarity	NPD7790	Approved
0.6154	Remote Similarity	NPD7789	Approved
0.6154	Remote Similarity	NPD7791	Approved
0.6154	Remote Similarity	NPD7953	Approved
0.6154	Remote Similarity	NPD7950	Approved
0.6154	Remote Similarity	NPD7951	Approved
0.6154	Remote Similarity	NPD6625	Approved
0.6147	Remote Similarity	NPD7731	Approved
0.6147	Remote Similarity	NPD7730	Approved
0.6146	Remote Similarity	NPD3782	Discontinued
0.6146	Remote Similarity	NPD7775	Approved
0.6146	Remote Similarity	NPD7881	Approved
0.6143	Remote Similarity	NPD7301	Phase 3
0.6143	Remote Similarity	NPD3888	Discontinued
0.614	Remote Similarity	NPD4420	Approved
0.6136	Remote Similarity	NPD4596	Phase 1
0.6134	Remote Similarity	NPD3399	Approved
0.613	Remote Similarity	NPD7271	Approved
0.6129	Remote Similarity	NPD2670	Approved
0.6126	Remote Similarity	NPD3372	Discontinued
0.6126	Remote Similarity	NPD5860	Discontinued
0.6124	Remote Similarity	NPD8459	Approved
0.6124	Remote Similarity	NPD8460	Approved
0.6119	Remote Similarity	NPD5426	Phase 3
0.6117	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD5928	Phase 1
0.6114	Remote Similarity	NPD2565	Phase 2
0.6114	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD2564	Approved
0.6113	Remote Similarity	NPD7956	Approved
0.6113	Remote Similarity	NPD7955	Approved
0.6111	Remote Similarity	NPD2506	Approved
0.6109	Remote Similarity	NPD7302	Phase 3
0.6109	Remote Similarity	NPD7300	Phase 3
0.6108	Remote Similarity	NPD4685	Phase 3
0.6108	Remote Similarity	NPD4684	Phase 3
0.6108	Remote Similarity	NPD4686	Approved
0.6105	Remote Similarity	NPD2435	Approved
0.6103	Remote Similarity	NPD5610	Approved
0.6099	Remote Similarity	NPD5263	Approved
0.6099	Remote Similarity	NPD7470	Discontinued
0.6098	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD3170	Approved
0.6096	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD5183	Approved
0.6089	Remote Similarity	NPD5186	Approved
0.6087	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD6723	Discontinued
0.6082	Remote Similarity	NPD5982	Phase 2
0.6077	Remote Similarity	NPD6557	Phase 2
0.6073	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD7205	Discontinued
0.6073	Remote Similarity	NPD7295	Approved
0.6065	Remote Similarity	NPD5071	Phase 2
0.6062	Remote Similarity	NPD8426	Approved
0.6062	Remote Similarity	NPD8425	Approved
0.6062	Remote Similarity	NPD4682	Phase 2
0.6056	Remote Similarity	NPD7569	Approved
0.6056	Remote Similarity	NPD7803	Approved
0.6056	Remote Similarity	NPD7570	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