NPASS Compound

Structure

NPC472114 OpenBabel07101719132D 25 29 0 0 1 0 0 0 0 0999 V2000 0.9485 0.2950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4759 1.4234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1282 -0.2770 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 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5543 0.9605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6203 -0.5398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7773 0.1473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7888 1.2348 0.0000 C 0 0 1 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 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0971 0.8073 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7456 1.3457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 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 0.7008 2.3447 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 -2.2226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6332 0.8850 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 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 14 2 0 0 0 0 7 15 2 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 13 10 1 6 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 21 1 1 0 0 0 17 19 1 1 0 0 0 17 22 1 0 0 0 0 18 20 1 1 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.18
Volume:	346.876
LogP:	2.563
LogD:	2.492
LogS:	-3.885
# Rotatable Bonds:	2
TPSA:	53.01
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.622
Synthetic Accessibility Score:	5.21
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.862
MDCK Permeability:	3.7009045627200976e-05
Pgp-inhibitor:	0.285
Pgp-substrate:	0.667
Human Intestinal Absorption (HIA):	0.81
20% Bioavailability (F20%):	0.341
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.541
Plasma Protein Binding (PPB):	45.6214485168457%
Volume Distribution (VD):	1.481
Pgp-substrate:	66.18230438232422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.08
CYP2C19-inhibitor:	0.078
CYP2C19-substrate:	0.806
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.102
CYP2D6-inhibitor:	0.042
CYP2D6-substrate:	0.243
CYP3A4-inhibitor:	0.107
CYP3A4-substrate:	0.646

ADMET: Excretion

Clearance (CL):	11.436
Half-life (T1/2):	0.075

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.797
Drug-inuced Liver Injury (DILI):	0.358
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.937
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.421
Carcinogencity:	0.917
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.887

Download Data

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

Natural Product: NPC472114

Natural Product ID:	NPC472114
*Common Name:**	IRQPOCSSDBXPGE-CYQMXNMFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IRQPOCSSDBXPGE-CYQMXNMFSA-N
Standard InCHI:	InChI=1S/C20H24N2O3/c1-3-12-11-21-9-8-20(24)14-6-4-5-7-15(14)22-17(19(23)25-2)13(12)10-16(21)18(20)22/h3-7,13,16-18,24H,8-11H2,1-2H3/b12-3-/t13-,16-,17-,18+,20-/m0/s1
SMILES:	CC=C1CN2CCC3(C4C2CC1C(N4C5=CC=CC=C53)C(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338237
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[506702]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[506702]

☑ 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 NPC472114 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	228
0.1-0.2	1008
0.2-0.3	3844
0.3-0.4	14043
0.4-0.5	16990
0.5-0.6	5272
0.6-0.7	1171
0.7-0.8	135
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472115
0.8428	Intermediate Similarity	NPC478076
0.8333	Intermediate Similarity	NPC476441
0.8107	Intermediate Similarity	NPC476425
0.8012	Intermediate Similarity	NPC85651
0.8	Intermediate Similarity	NPC471122
0.7931	Intermediate Similarity	NPC476428
0.7844	Intermediate Similarity	NPC474058
0.7811	Intermediate Similarity	NPC471124
0.7784	Intermediate Similarity	NPC143533
0.7759	Intermediate Similarity	NPC476326
0.7725	Intermediate Similarity	NPC153694
0.7725	Intermediate Similarity	NPC211525
0.7709	Intermediate Similarity	NPC21425
0.7679	Intermediate Similarity	NPC36495
0.7661	Intermediate Similarity	NPC278887
0.765	Intermediate Similarity	NPC57994
0.765	Intermediate Similarity	NPC289299
0.7602	Intermediate Similarity	NPC472106
0.7574	Intermediate Similarity	NPC243673
0.7574	Intermediate Similarity	NPC310403
0.7574	Intermediate Similarity	NPC263709
0.7574	Intermediate Similarity	NPC148468
0.7574	Intermediate Similarity	NPC63210
0.7574	Intermediate Similarity	NPC97380
0.7572	Intermediate Similarity	NPC472118
0.7529	Intermediate Similarity	NPC225319
0.7515	Intermediate Similarity	NPC113946
0.75	Intermediate Similarity	NPC52059
0.75	Intermediate Similarity	NPC470069
0.7485	Intermediate Similarity	NPC99632
0.7485	Intermediate Similarity	NPC476231
0.7485	Intermediate Similarity	NPC472120
0.7485	Intermediate Similarity	NPC472101
0.7485	Intermediate Similarity	NPC282339
0.7472	Intermediate Similarity	NPC166169
0.7471	Intermediate Similarity	NPC193410
0.7456	Intermediate Similarity	NPC29285
0.7442	Intermediate Similarity	NPC313757
0.743	Intermediate Similarity	NPC475962
0.7427	Intermediate Similarity	NPC248117
0.7419	Intermediate Similarity	NPC472116
0.7416	Intermediate Similarity	NPC99043
0.7416	Intermediate Similarity	NPC218594
0.7416	Intermediate Similarity	NPC321211
0.7412	Intermediate Similarity	NPC61013
0.7401	Intermediate Similarity	NPC129624
0.7396	Intermediate Similarity	NPC161827
0.7386	Intermediate Similarity	NPC276993
0.7386	Intermediate Similarity	NPC181138
0.7386	Intermediate Similarity	NPC21752
0.7386	Intermediate Similarity	NPC298851
0.7386	Intermediate Similarity	NPC293255
0.7386	Intermediate Similarity	NPC210415
0.7384	Intermediate Similarity	NPC472117
0.7371	Intermediate Similarity	NPC469915
0.7363	Intermediate Similarity	NPC478077
0.7322	Intermediate Similarity	NPC472323
0.7322	Intermediate Similarity	NPC181928
0.7314	Intermediate Similarity	NPC223595
0.7314	Intermediate Similarity	NPC167724
0.7314	Intermediate Similarity	NPC224970
0.7303	Intermediate Similarity	NPC203202
0.7303	Intermediate Similarity	NPC264482
0.7301	Intermediate Similarity	NPC470301
0.7297	Intermediate Similarity	NPC25401
0.7297	Intermediate Similarity	NPC203628
0.7297	Intermediate Similarity	NPC28510
0.7293	Intermediate Similarity	NPC159963
0.7288	Intermediate Similarity	NPC139085
0.7288	Intermediate Similarity	NPC251212
0.7288	Intermediate Similarity	NPC214626
0.7288	Intermediate Similarity	NPC285622
0.7287	Intermediate Similarity	NPC90967
0.7278	Intermediate Similarity	NPC15840
0.7249	Intermediate Similarity	NPC265642
0.7249	Intermediate Similarity	NPC218733
0.7249	Intermediate Similarity	NPC138615
0.7249	Intermediate Similarity	NPC132874
0.7249	Intermediate Similarity	NPC52557
0.7243	Intermediate Similarity	NPC473298
0.7243	Intermediate Similarity	NPC105055
0.7243	Intermediate Similarity	NPC22689
0.7243	Intermediate Similarity	NPC5630
0.7213	Intermediate Similarity	NPC322621
0.7209	Intermediate Similarity	NPC123241
0.7198	Intermediate Similarity	NPC477159
0.7196	Intermediate Similarity	NPC472541
0.7196	Intermediate Similarity	NPC472542
0.7188	Intermediate Similarity	NPC1464
0.7188	Intermediate Similarity	NPC471436
0.7184	Intermediate Similarity	NPC472121
0.7184	Intermediate Similarity	NPC176983
0.7184	Intermediate Similarity	NPC293458
0.717	Intermediate Similarity	NPC314098
0.7158	Intermediate Similarity	NPC97584
0.7158	Intermediate Similarity	NPC302235
0.7158	Intermediate Similarity	NPC472119
0.7151	Intermediate Similarity	NPC470548
0.7143	Intermediate Similarity	NPC245916
0.7143	Intermediate Similarity	NPC303214
0.7143	Intermediate Similarity	NPC472539
0.7143	Intermediate Similarity	NPC470787
0.7143	Intermediate Similarity	NPC472540
0.7135	Intermediate Similarity	NPC14994
0.7135	Intermediate Similarity	NPC473815
0.7127	Intermediate Similarity	NPC6974
0.7126	Intermediate Similarity	NPC309531
0.7126	Intermediate Similarity	NPC472102
0.712	Intermediate Similarity	NPC472107
0.712	Intermediate Similarity	NPC472209
0.712	Intermediate Similarity	NPC79062
0.712	Intermediate Similarity	NPC52262
0.7097	Intermediate Similarity	NPC175474
0.7093	Intermediate Similarity	NPC473297
0.709	Intermediate Similarity	NPC34717
0.709	Intermediate Similarity	NPC221687
0.7088	Intermediate Similarity	NPC469896
0.7085	Intermediate Similarity	NPC471663
0.7083	Intermediate Similarity	NPC472100
0.7077	Intermediate Similarity	NPC246140
0.7077	Intermediate Similarity	NPC195787
0.7072	Intermediate Similarity	NPC186669
0.7072	Intermediate Similarity	NPC260075
0.7065	Intermediate Similarity	NPC258480
0.7062	Intermediate Similarity	NPC279527
0.7062	Intermediate Similarity	NPC214960
0.7041	Intermediate Similarity	NPC478075
0.7037	Intermediate Similarity	NPC203972
0.7033	Intermediate Similarity	NPC219336
0.7027	Intermediate Similarity	NPC469460
0.7022	Intermediate Similarity	NPC469462
0.7021	Intermediate Similarity	NPC472097
0.7016	Intermediate Similarity	NPC469736
0.7015	Intermediate Similarity	NPC234772
0.7011	Intermediate Similarity	NPC470317
0.7011	Intermediate Similarity	NPC104345
0.7005	Intermediate Similarity	NPC284706
0.7	Intermediate Similarity	NPC242000
0.7	Intermediate Similarity	NPC96901
0.6995	Remote Similarity	NPC81654
0.6995	Remote Similarity	NPC313985
0.6995	Remote Similarity	NPC79129
0.6995	Remote Similarity	NPC39822
0.6995	Remote Similarity	NPC249150
0.6995	Remote Similarity	NPC195461
0.6995	Remote Similarity	NPC49196
0.6989	Remote Similarity	NPC66210
0.6988	Remote Similarity	NPC43477
0.6984	Remote Similarity	NPC204970
0.6978	Remote Similarity	NPC217372
0.6978	Remote Similarity	NPC15573
0.6978	Remote Similarity	NPC183662
0.6974	Remote Similarity	NPC477179
0.6974	Remote Similarity	NPC476098
0.6971	Remote Similarity	NPC33949
0.6968	Remote Similarity	NPC473569
0.6968	Remote Similarity	NPC474059
0.6963	Remote Similarity	NPC473375
0.6963	Remote Similarity	NPC97100
0.6961	Remote Similarity	NPC469726
0.6961	Remote Similarity	NPC329338
0.6959	Remote Similarity	NPC232600
0.6959	Remote Similarity	NPC469732
0.6959	Remote Similarity	NPC473329
0.6944	Remote Similarity	NPC318183
0.6941	Remote Similarity	NPC254798
0.6939	Remote Similarity	NPC477180
0.6939	Remote Similarity	NPC254850
0.6939	Remote Similarity	NPC477178
0.6939	Remote Similarity	NPC477181
0.6931	Remote Similarity	NPC22476
0.6927	Remote Similarity	NPC33507
0.6923	Remote Similarity	NPC57398
0.6919	Remote Similarity	NPC472104
0.6919	Remote Similarity	NPC471945
0.6919	Remote Similarity	NPC471950
0.6915	Remote Similarity	NPC63199
0.6915	Remote Similarity	NPC102338
0.6915	Remote Similarity	NPC196251
0.6915	Remote Similarity	NPC111602
0.6912	Remote Similarity	NPC475609
0.6907	Remote Similarity	NPC67904
0.6907	Remote Similarity	NPC138830
0.6905	Remote Similarity	NPC308197
0.6904	Remote Similarity	NPC470490
0.6904	Remote Similarity	NPC477173
0.6904	Remote Similarity	NPC477174
0.6902	Remote Similarity	NPC11149
0.6902	Remote Similarity	NPC475685
0.6893	Remote Similarity	NPC286871
0.6891	Remote Similarity	NPC50503
0.6888	Remote Similarity	NPC295548
0.6885	Remote Similarity	NPC474081
0.6884	Remote Similarity	NPC471946
0.6884	Remote Similarity	NPC471951
0.6878	Remote Similarity	NPC472112
0.6872	Remote Similarity	NPC471512
0.6869	Remote Similarity	NPC470488
0.6869	Remote Similarity	NPC472538

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 NPC472114 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	444
0.2-0.3	729
0.3-0.4	1264
0.4-0.5	2905
0.5-0.6	2914
0.6-0.7	719
0.7-0.8	23
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
0.7709	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4121	Phase 3
0.7651	Intermediate Similarity	NPD4120	Approved
0.765	Intermediate Similarity	NPD4602	Approved
0.7605	Intermediate Similarity	NPD5743	Approved
0.7605	Intermediate Similarity	NPD5742	Approved
0.7605	Intermediate Similarity	NPD5741	Approved
0.7202	Intermediate Similarity	NPD5942	Approved
0.7202	Intermediate Similarity	NPD5941	Approved
0.7168	Intermediate Similarity	NPD7599	Phase 2
0.7143	Intermediate Similarity	NPD4520	Approved
0.7126	Intermediate Similarity	NPD7600	Phase 2
0.7108	Intermediate Similarity	NPD5024	Approved
0.7101	Intermediate Similarity	NPD4682	Phase 2
0.7088	Intermediate Similarity	NPD6833	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6320	Approved
0.7056	Intermediate Similarity	NPD5466	Approved
0.7041	Intermediate Similarity	NPD1802	Approved
0.7041	Intermediate Similarity	NPD1801	Approved
0.7019	Intermediate Similarity	NPD4619	Approved
0.7019	Intermediate Similarity	NPD4621	Approved
0.7012	Intermediate Similarity	NPD2670	Approved
0.7011	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4600	Approved
0.6995	Remote Similarity	NPD4601	Approved
0.6988	Remote Similarity	NPD3625	Discontinued
0.6961	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5120	Approved
0.6933	Remote Similarity	NPD5119	Approved
0.6933	Remote Similarity	NPD5121	Approved
0.6932	Remote Similarity	NPD2506	Approved
0.6923	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6017	Discontinued
0.6914	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD3377	Discontinued
0.6906	Remote Similarity	NPD5997	Discontinued
0.6905	Remote Similarity	NPD2820	Phase 3
0.6902	Remote Similarity	NPD6878	Phase 2
0.6902	Remote Similarity	NPD6879	Phase 2
0.6895	Remote Similarity	NPD6665	Discontinued
0.6895	Remote Similarity	NPD7570	Approved
0.6895	Remote Similarity	NPD7569	Approved
0.6894	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5993	Phase 1
0.6868	Remote Similarity	NPD3422	Phase 3
0.6868	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD3423	Phase 2
0.6854	Remote Similarity	NPD3790	Phase 2
0.6848	Remote Similarity	NPD6073	Approved
0.6845	Remote Similarity	NPD2365	Approved
0.6839	Remote Similarity	NPD2994	Approved
0.6834	Remote Similarity	NPD4082	Approved
0.6824	Remote Similarity	NPD5932	Phase 3
0.6824	Remote Similarity	NPD5931	Phase 3
0.6824	Remote Similarity	NPD5933	Phase 3
0.6821	Remote Similarity	NPD4500	Approved
0.6821	Remote Similarity	NPD6805	Discontinued
0.6821	Remote Similarity	NPD4501	Approved
0.6816	Remote Similarity	NPD5430	Discontinued
0.6811	Remote Similarity	NPD4329	Approved
0.6811	Remote Similarity	NPD4330	Approved
0.6805	Remote Similarity	NPD4430	Phase 2
0.6802	Remote Similarity	NPD4432	Discontinued
0.6802	Remote Similarity	NPD7205	Discontinued
0.6796	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5263	Approved
0.6788	Remote Similarity	NPD2791	Discontinued
0.6786	Remote Similarity	NPD6238	Discontinued
0.6784	Remote Similarity	NPD6416	Phase 2
0.678	Remote Similarity	NPD2427	Approved
0.678	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2116	Approved
0.6774	Remote Similarity	NPD2115	Approved
0.6774	Remote Similarity	NPD2117	Pre-registration
0.6768	Remote Similarity	NPD1527	Phase 2
0.6766	Remote Similarity	NPD5860	Discontinued
0.6766	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1109	Approved
0.6766	Remote Similarity	NPD1110	Approved
0.6766	Remote Similarity	NPD3170	Approved
0.6761	Remote Similarity	NPD7105	Phase 1
0.6758	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6557	Phase 2
0.6753	Remote Similarity	NPD5003	Discontinued
0.675	Remote Similarity	NPD2907	Approved
0.675	Remote Similarity	NPD2906	Approved
0.674	Remote Similarity	NPD2037	Approved
0.6737	Remote Similarity	NPD8025	Phase 2
0.6737	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD3663	Approved
0.6728	Remote Similarity	NPD3661	Approved
0.6728	Remote Similarity	NPD3662	Phase 3
0.6728	Remote Similarity	NPD3664	Approved
0.6728	Remote Similarity	NPD5204	Approved
0.6727	Remote Similarity	NPD5185	Approved
0.6727	Remote Similarity	NPD6309	Approved
0.6727	Remote Similarity	NPD5182	Approved
0.6727	Remote Similarity	NPD6310	Approved
0.6727	Remote Similarity	NPD5184	Approved
0.6727	Remote Similarity	NPD6311	Approved
0.6721	Remote Similarity	NPD7854	Phase 2
0.6718	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2946	Phase 2
0.6708	Remote Similarity	NPD2160	Approved
0.6708	Remote Similarity	NPD2626	Approved
0.6708	Remote Similarity	NPD2159	Approved
0.6708	Remote Similarity	NPD2627	Approved
0.6708	Remote Similarity	NPD2628	Approved
0.6708	Remote Similarity	NPD2625	Approved
0.6707	Remote Similarity	NPD6295	Approved
0.6707	Remote Similarity	NPD6294	Approved
0.6705	Remote Similarity	NPD4888	Discontinued
0.6703	Remote Similarity	NPD3792	Approved
0.6703	Remote Similarity	NPD5498	Phase 2
0.6701	Remote Similarity	NPD6321	Discontinued
0.67	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4492	Approved
0.67	Remote Similarity	NPD4494	Approved
0.6688	Remote Similarity	NPD3030	Approved
0.6688	Remote Similarity	NPD3032	Approved
0.6688	Remote Similarity	NPD3031	Approved
0.6687	Remote Similarity	NPD5201	Approved
0.6687	Remote Similarity	NPD4617	Approved
0.6687	Remote Similarity	NPD4620	Approved
0.6687	Remote Similarity	NPD5203	Approved
0.6685	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3470	Approved
0.6684	Remote Similarity	NPD3471	Approved
0.6667	Remote Similarity	NPD2612	Approved
0.6667	Remote Similarity	NPD2608	Approved
0.6667	Remote Similarity	NPD3132	Approved
0.6667	Remote Similarity	NPD2609	Approved
0.6667	Remote Similarity	NPD4216	Approved
0.6667	Remote Similarity	NPD3828	Approved
0.6667	Remote Similarity	NPD2611	Approved
0.6667	Remote Similarity	NPD2575	Approved
0.6667	Remote Similarity	NPD1405	Approved
0.6667	Remote Similarity	NPD3131	Approved
0.6667	Remote Similarity	NPD2431	Approved
0.6667	Remote Similarity	NPD5504	Discontinued
0.6667	Remote Similarity	NPD4150	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4215	Approved
0.6667	Remote Similarity	NPD2432	Approved
0.6667	Remote Similarity	NPD2610	Approved
0.6667	Remote Similarity	NPD4218	Approved
0.6667	Remote Similarity	NPD5042	Phase 1
0.6667	Remote Similarity	NPD4217	Approved
0.665	Remote Similarity	NPD4493	Discontinued
0.665	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2455	Approved
0.6648	Remote Similarity	NPD7126	Discontinued
0.6648	Remote Similarity	NPD2454	Approved
0.6648	Remote Similarity	NPD2844	Phase 3
0.6647	Remote Similarity	NPD5725	Approved
0.6646	Remote Similarity	NPD1069	Approved
0.6646	Remote Similarity	NPD1070	Approved
0.6631	Remote Similarity	NPD5445	Approved
0.6631	Remote Similarity	NPD6452	Discontinued
0.6631	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4175	Approved
0.6626	Remote Similarity	NPD4177	Approved
0.6625	Remote Similarity	NPD1360	Approved
0.6615	Remote Similarity	NPD2564	Approved
0.6615	Remote Similarity	NPD5928	Phase 1
0.6615	Remote Similarity	NPD2565	Phase 2
0.6615	Remote Similarity	NPD4499	Approved
0.6609	Remote Similarity	NPD4161	Discontinued
0.6609	Remote Similarity	NPD7528	Approved
0.6608	Remote Similarity	NPD6301	Phase 2
0.6608	Remote Similarity	NPD1625	Approved
0.6607	Remote Similarity	NPD2567	Approved
0.6607	Remote Similarity	NPD2569	Approved
0.6606	Remote Similarity	NPD5581	Approved
0.6603	Remote Similarity	NPD6070	Approved
0.6603	Remote Similarity	NPD6069	Approved
0.66	Remote Similarity	NPD1294	Discontinued
0.6598	Remote Similarity	NPD5610	Approved
0.6593	Remote Similarity	NPD5823	Approved
0.6592	Remote Similarity	NPD4485	Approved
0.6592	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD2613	Approved
0.6585	Remote Similarity	NPD4676	Approved
0.6583	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.658	Remote Similarity	NPD6659	Phase 2
0.658	Remote Similarity	NPD4370	Phase 3
0.6579	Remote Similarity	NPD6227	Discontinued
0.6578	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD3782	Discontinued
0.6575	Remote Similarity	NPD7734	Approved
0.6573	Remote Similarity	NPD1663	Discontinued
0.6571	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.657	Remote Similarity	NPD2387	Approved
0.6566	Remote Similarity	NPD3614	Approved
0.6566	Remote Similarity	NPD3616	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