NPASS Compound

Structure

NPC472100 OpenBabel07101718242D 24 28 0 0 1 0 0 0 0 0999 V2000 5.4044 -3.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7572 -2.6783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3968 -2.1371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1444 -0.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5627 -1.5913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0041 -1.9405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7353 -2.4704 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0880 -1.9351 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3611 -1.2688 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0104 -0.6399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8080 -1.7226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 1 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 2.8025 -1.6180 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 5.0443 -1.5193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3842 -1.9272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 14 2 0 0 0 0 5 15 2 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 7 17 1 0 0 0 0 8 16 1 0 0 0 0 9 24 1 0 0 0 0 10 21 1 0 0 0 0 10 24 1 0 0 0 0 11 22 1 0 0 0 0 12 6 1 6 0 0 0 12 13 1 0 0 0 0 13 9 1 6 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 6 0 0 0 17 19 1 1 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 20 2 0 0 0 0 18 23 1 0 0 0 0 19 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.18
Volume:	332.216
LogP:	1.634
LogD:	1.888
LogS:	-3.441
# Rotatable Bonds:	2
TPSA:	61.8
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.868
Synthetic Accessibility Score:	6.194
Fsp3:	0.632
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:	-5.168
MDCK Permeability:	2.7751557354349643e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.963
Human Intestinal Absorption (HIA):	0.499
20% Bioavailability (F20%):	0.752
30% Bioavailability (F30%):	0.284

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.775
Plasma Protein Binding (PPB):	30.973628997802734%
Volume Distribution (VD):	1.406
Pgp-substrate:	64.69659423828125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.254
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.887
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.118
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.62
CYP3A4-inhibitor:	0.117
CYP3A4-substrate:	0.774

ADMET: Excretion

Clearance (CL):	8.624
Half-life (T1/2):	0.537

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.839
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.379
Rat Oral Acute Toxicity:	0.225
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.372
Carcinogencity:	0.72
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC472100

Natural Product ID:	NPC472100
*Common Name:**	PYNJMVMYCWTBLH-TVHUVIFXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PYNJMVMYCWTBLH-TVHUVIFXSA-N
Standard InCHI:	InChI=1S/C19H24N2O3/c1-11(22)6-12-7-17-19(8-16-13(12)9-24-10-21(16)17)14-4-2-3-5-15(14)20-18(19)23/h2-5,11-13,16-17,22H,6-10H2,1H3,(H,20,23)/t11?,12-,13-,16+,17+,19-/m1/s1
SMILES:	CC(CC1CC2C3(CC4C1COCN24)C5=CC=CC=C5NC3=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338223
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001146] Indolines

*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[543305]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[543305]

☑ 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 NPC472100 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	207
0.1-0.2	1051
0.2-0.3	3018
0.3-0.4	18758
0.4-0.5	13774
0.5-0.6	4931
0.6-0.7	839
0.7-0.8	100
0.8-0.85	15
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9149	High Similarity	NPC472103
0.8581	High Similarity	NPC469462
0.8543	High Similarity	NPC477157
0.8543	High Similarity	NPC477156
0.8472	Intermediate Similarity	NPC243162
0.8302	Intermediate Similarity	NPC210415
0.8302	Intermediate Similarity	NPC276993
0.8302	Intermediate Similarity	NPC181138
0.8302	Intermediate Similarity	NPC21752
0.8302	Intermediate Similarity	NPC293255
0.8302	Intermediate Similarity	NPC298851
0.8258	Intermediate Similarity	NPC477158
0.8129	Intermediate Similarity	NPC153694
0.8129	Intermediate Similarity	NPC211525
0.8089	Intermediate Similarity	NPC472101
0.8089	Intermediate Similarity	NPC472120
0.8089	Intermediate Similarity	NPC472121
0.8077	Intermediate Similarity	NPC263709
0.8077	Intermediate Similarity	NPC310403
0.8077	Intermediate Similarity	NPC97380
0.8077	Intermediate Similarity	NPC243673
0.8077	Intermediate Similarity	NPC63210
0.8077	Intermediate Similarity	NPC148468
0.7987	Intermediate Similarity	NPC52059
0.7987	Intermediate Similarity	NPC470069
0.7947	Intermediate Similarity	NPC116519
0.7892	Intermediate Similarity	NPC475962
0.7885	Intermediate Similarity	NPC161827
0.7848	Intermediate Similarity	NPC469461
0.7764	Intermediate Similarity	NPC472106
0.7647	Intermediate Similarity	NPC469460
0.7586	Intermediate Similarity	NPC478079
0.7548	Intermediate Similarity	NPC264589
0.7545	Intermediate Similarity	NPC476441
0.7545	Intermediate Similarity	NPC472122
0.7545	Intermediate Similarity	NPC24594
0.7531	Intermediate Similarity	NPC472117
0.7531	Intermediate Similarity	NPC85651
0.7514	Intermediate Similarity	NPC217294
0.75	Intermediate Similarity	NPC29285
0.75	Intermediate Similarity	NPC278887
0.7469	Intermediate Similarity	NPC143457
0.7469	Intermediate Similarity	NPC309531
0.7469	Intermediate Similarity	NPC472102
0.7447	Intermediate Similarity	NPC264580
0.7427	Intermediate Similarity	NPC98197
0.7412	Intermediate Similarity	NPC472105
0.7412	Intermediate Similarity	NPC187827
0.7396	Intermediate Similarity	NPC326575
0.7358	Intermediate Similarity	NPC475763
0.7353	Intermediate Similarity	NPC133261
0.7346	Intermediate Similarity	NPC113946
0.7341	Intermediate Similarity	NPC472209
0.7329	Intermediate Similarity	NPC325013
0.7326	Intermediate Similarity	NPC472110
0.7326	Intermediate Similarity	NPC139291
0.7326	Intermediate Similarity	NPC472108
0.7326	Intermediate Similarity	NPC472109
0.7318	Intermediate Similarity	NPC475559
0.7286	Intermediate Similarity	NPC470550
0.7283	Intermediate Similarity	NPC245741
0.7222	Intermediate Similarity	NPC473297
0.7219	Intermediate Similarity	NPC476425
0.7212	Intermediate Similarity	NPC176983
0.72	Intermediate Similarity	NPC291759
0.7179	Intermediate Similarity	NPC477155
0.7176	Intermediate Similarity	NPC13367
0.7175	Intermediate Similarity	NPC105055
0.7175	Intermediate Similarity	NPC22689
0.7168	Intermediate Similarity	NPC476428
0.716	Intermediate Similarity	NPC478076
0.7151	Intermediate Similarity	NPC99043
0.7151	Intermediate Similarity	NPC218594
0.7143	Intermediate Similarity	NPC133591
0.7143	Intermediate Similarity	NPC317430
0.7127	Intermediate Similarity	NPC302548
0.7126	Intermediate Similarity	NPC70172
0.7126	Intermediate Similarity	NPC19679
0.712	Intermediate Similarity	NPC474077
0.7118	Intermediate Similarity	NPC473880
0.7102	Intermediate Similarity	NPC282092
0.7102	Intermediate Similarity	NPC38823
0.7102	Intermediate Similarity	NPC207033
0.7083	Intermediate Similarity	NPC472115
0.7083	Intermediate Similarity	NPC472114
0.7063	Intermediate Similarity	NPC212799
0.7048	Intermediate Similarity	NPC255229
0.7048	Intermediate Similarity	NPC81229
0.7048	Intermediate Similarity	NPC474058
0.7042	Intermediate Similarity	NPC205652
0.7029	Intermediate Similarity	NPC477159
0.7029	Intermediate Similarity	NPC472104
0.7018	Intermediate Similarity	NPC472123
0.7011	Intermediate Similarity	NPC15840
0.7006	Intermediate Similarity	NPC286871
0.7	Intermediate Similarity	NPC472118
0.6984	Remote Similarity	NPC168250
0.6981	Remote Similarity	NPC311330
0.6975	Remote Similarity	NPC318086
0.6959	Remote Similarity	NPC158129
0.6954	Remote Similarity	NPC259098
0.6954	Remote Similarity	NPC197680
0.6949	Remote Similarity	NPC62510
0.6944	Remote Similarity	NPC470483
0.6944	Remote Similarity	NPC147957
0.694	Remote Similarity	NPC272706
0.6936	Remote Similarity	NPC264482
0.6936	Remote Similarity	NPC203202
0.6923	Remote Similarity	NPC475420
0.6914	Remote Similarity	NPC39822
0.6908	Remote Similarity	NPC226662
0.6906	Remote Similarity	NPC204970
0.6897	Remote Similarity	NPC476326
0.6893	Remote Similarity	NPC472294
0.6893	Remote Similarity	NPC97584
0.6889	Remote Similarity	NPC469501
0.6889	Remote Similarity	NPC174629
0.6889	Remote Similarity	NPC469470
0.6879	Remote Similarity	NPC189812
0.6879	Remote Similarity	NPC329688
0.6868	Remote Similarity	NPC470485
0.6868	Remote Similarity	NPC203972
0.6864	Remote Similarity	NPC469541
0.6861	Remote Similarity	NPC178681
0.6851	Remote Similarity	NPC28510
0.6839	Remote Similarity	NPC134586
0.6839	Remote Similarity	NPC129624
0.6837	Remote Similarity	NPC108826
0.6825	Remote Similarity	NPC472111
0.6821	Remote Similarity	NPC251212
0.6821	Remote Similarity	NPC139085
0.6821	Remote Similarity	NPC214626
0.68	Remote Similarity	NPC211997
0.6786	Remote Similarity	NPC471122
0.6784	Remote Similarity	NPC279527
0.6784	Remote Similarity	NPC214960
0.6782	Remote Similarity	NPC475097
0.6778	Remote Similarity	NPC472323
0.6765	Remote Similarity	NPC313757
0.6761	Remote Similarity	NPC6974
0.676	Remote Similarity	NPC476095
0.6758	Remote Similarity	NPC472097
0.6757	Remote Similarity	NPC90967
0.6746	Remote Similarity	NPC315368
0.6746	Remote Similarity	NPC225319
0.6746	Remote Similarity	NPC68650
0.6742	Remote Similarity	NPC256288
0.6742	Remote Similarity	NPC159963
0.6738	Remote Similarity	NPC475489
0.6733	Remote Similarity	NPC283130
0.6733	Remote Similarity	NPC328683
0.6731	Remote Similarity	NPC184437
0.6724	Remote Similarity	NPC473743
0.6706	Remote Similarity	NPC282339
0.6706	Remote Similarity	NPC476231
0.6706	Remote Similarity	NPC99632
0.6705	Remote Similarity	NPC186669
0.6704	Remote Similarity	NPC2933
0.6704	Remote Similarity	NPC472119
0.6703	Remote Similarity	NPC95783
0.6689	Remote Similarity	NPC317758
0.6687	Remote Similarity	NPC186284
0.6687	Remote Similarity	NPC22082
0.6686	Remote Similarity	NPC472586
0.6686	Remote Similarity	NPC36495
0.6685	Remote Similarity	NPC181928
0.6685	Remote Similarity	NPC285841
0.6667	Remote Similarity	NPC259626
0.6667	Remote Similarity	NPC472107
0.6667	Remote Similarity	NPC10730
0.6667	Remote Similarity	NPC10875
0.6667	Remote Similarity	NPC25401
0.6667	Remote Similarity	NPC472443
0.6667	Remote Similarity	NPC473007
0.6667	Remote Similarity	NPC52262
0.6667	Remote Similarity	NPC79062
0.6649	Remote Similarity	NPC249040
0.6648	Remote Similarity	NPC472444
0.6648	Remote Similarity	NPC150048
0.6648	Remote Similarity	NPC320147
0.6648	Remote Similarity	NPC203754
0.6631	Remote Similarity	NPC52557
0.663	Remote Similarity	NPC473615
0.6628	Remote Similarity	NPC471124
0.6627	Remote Similarity	NPC129721
0.6626	Remote Similarity	NPC470824
0.6623	Remote Similarity	NPC101372
0.6623	Remote Similarity	NPC295478
0.6612	Remote Similarity	NPC473298
0.6611	Remote Similarity	NPC258480
0.661	Remote Similarity	NPC260075
0.6609	Remote Similarity	NPC257354
0.6597	Remote Similarity	NPC14339
0.6593	Remote Similarity	NPC14994
0.6593	Remote Similarity	NPC229484
0.6588	Remote Similarity	NPC193410
0.6581	Remote Similarity	NPC69496
0.658	Remote Similarity	NPC329329
0.658	Remote Similarity	NPC317709
0.6579	Remote Similarity	NPC52801

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 NPC472100 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	459
0.2-0.3	605
0.3-0.4	1333
0.4-0.5	3431
0.5-0.6	2778
0.6-0.7	389
0.7-0.8	11
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8411	Intermediate Similarity	NPD4121	Phase 3
0.8411	Intermediate Similarity	NPD4120	Approved
0.8355	Intermediate Similarity	NPD5741	Approved
0.8355	Intermediate Similarity	NPD5742	Approved
0.8355	Intermediate Similarity	NPD5743	Approved
0.7597	Intermediate Similarity	NPD5595	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD2210	Approved
0.7518	Intermediate Similarity	NPD2212	Approved
0.7427	Intermediate Similarity	NPD7252	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5881	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2622	Approved
0.7092	Intermediate Similarity	NPD3148	Approved
0.7092	Intermediate Similarity	NPD3150	Approved
0.7092	Intermediate Similarity	NPD2658	Approved
0.7092	Intermediate Similarity	NPD3149	Approved
0.7092	Intermediate Similarity	NPD2659	Approved
0.7092	Intermediate Similarity	NPD3147	Approved
0.7037	Intermediate Similarity	NPD3329	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1762	Approved
0.7021	Intermediate Similarity	NPD1764	Approved
0.7014	Intermediate Similarity	NPD7522	Discontinued
0.6959	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5631	Phase 3
0.6875	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6301	Phase 2
0.6753	Remote Similarity	NPD4274	Approved
0.6753	Remote Similarity	NPD4275	Approved
0.6753	Remote Similarity	NPD3720	Discontinued
0.6742	Remote Similarity	NPD5596	Phase 2
0.6738	Remote Similarity	NPD2679	Approved
0.6738	Remote Similarity	NPD2678	Approved
0.6733	Remote Similarity	NPD478	Approved
0.6731	Remote Similarity	NPD5184	Approved
0.6731	Remote Similarity	NPD5182	Approved
0.6731	Remote Similarity	NPD5185	Approved
0.6685	Remote Similarity	NPD4951	Discontinued
0.6685	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4719	Phase 2
0.6647	Remote Similarity	NPD7600	Phase 2
0.6647	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6320	Approved
0.6629	Remote Similarity	NPD6879	Phase 2
0.6629	Remote Similarity	NPD6878	Phase 2
0.6625	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD7200	Approved
0.6623	Remote Similarity	NPD995	Clinical (unspecified phase)
0.662	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4682	Phase 2
0.6591	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD6789	Approved
0.6581	Remote Similarity	NPD2613	Approved
0.6577	Remote Similarity	NPD1922	Discontinued
0.6566	Remote Similarity	NPD6221	Approved
0.6566	Remote Similarity	NPD6222	Approved
0.6556	Remote Similarity	NPD4218	Approved
0.6556	Remote Similarity	NPD3131	Approved
0.6556	Remote Similarity	NPD4217	Approved
0.6556	Remote Similarity	NPD4216	Approved
0.6556	Remote Similarity	NPD4215	Approved
0.6556	Remote Similarity	NPD2609	Approved
0.6556	Remote Similarity	NPD2612	Approved
0.6556	Remote Similarity	NPD3132	Approved
0.6556	Remote Similarity	NPD2608	Approved
0.6556	Remote Similarity	NPD2610	Approved
0.6556	Remote Similarity	NPD2611	Approved
0.6552	Remote Similarity	NPD3983	Phase 3
0.6552	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD4796	Discontinued
0.6525	Remote Similarity	NPD5717	Approved
0.6512	Remote Similarity	NPD1742	Approved
0.6512	Remote Similarity	NPD19	Approved
0.6512	Remote Similarity	NPD1743	Approved
0.6509	Remote Similarity	NPD5617	Suspended
0.6506	Remote Similarity	NPD4703	Approved
0.6506	Remote Similarity	NPD4702	Approved
0.6503	Remote Similarity	NPD2383	Phase 1
0.6497	Remote Similarity	NPD865	Approved
0.6497	Remote Similarity	NPD864	Approved
0.6491	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7599	Phase 2
0.6488	Remote Similarity	NPD8400	Approved
0.6488	Remote Similarity	NPD8402	Approved
0.6488	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD8401	Approved
0.6481	Remote Similarity	NPD2093	Discontinued
0.6477	Remote Similarity	NPD2216	Approved
0.6477	Remote Similarity	NPD2215	Approved
0.6474	Remote Similarity	NPD4601	Approved
0.6474	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4600	Approved
0.6471	Remote Similarity	NPD4602	Approved
0.6461	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD2380	Approved
0.6461	Remote Similarity	NPD2381	Approved
0.6461	Remote Similarity	NPD2382	Approved
0.6458	Remote Similarity	NPD1107	Approved
0.6458	Remote Similarity	NPD4116	Approved
0.6458	Remote Similarity	NPD1108	Approved
0.6456	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD4745	Approved
0.6456	Remote Similarity	NPD2566	Approved
0.6456	Remote Similarity	NPD3090	Approved
0.6456	Remote Similarity	NPD4746	Phase 3
0.6456	Remote Similarity	NPD1594	Phase 3
0.6456	Remote Similarity	NPD8118	Discontinued
0.6456	Remote Similarity	NPD2574	Discontinued
0.6456	Remote Similarity	NPD2570	Approved
0.6456	Remote Similarity	NPD3087	Approved
0.6456	Remote Similarity	NPD1595	Approved
0.6456	Remote Similarity	NPD3616	Approved
0.6456	Remote Similarity	NPD3089	Approved
0.6456	Remote Similarity	NPD2571	Approved
0.6456	Remote Similarity	NPD3614	Approved
0.6456	Remote Similarity	NPD2573	Approved
0.6456	Remote Similarity	NPD3615	Approved
0.6456	Remote Similarity	NPD3088	Approved
0.6452	Remote Similarity	NPD6259	Discontinued
0.6447	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4165	Phase 2
0.6438	Remote Similarity	NPD3066	Phase 2
0.6434	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD1001	Discontinued
0.6432	Remote Similarity	NPD2843	Phase 2
0.6432	Remote Similarity	NPD2845	Phase 2
0.6429	Remote Similarity	NPD4119	Approved
0.6424	Remote Similarity	NPD7725	Approved
0.642	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD8020	Approved
0.6413	Remote Similarity	NPD8021	Approved
0.6405	Remote Similarity	NPD7461	Approved
0.6404	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD2188	Approved
0.6391	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD6158	Phase 2
0.6387	Remote Similarity	NPD4500	Approved
0.6387	Remote Similarity	NPD4501	Approved
0.6384	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5138	Approved
0.6379	Remote Similarity	NPD5140	Approved
0.6376	Remote Similarity	NPD6070	Approved
0.6376	Remote Similarity	NPD6069	Approved
0.6375	Remote Similarity	NPD4684	Phase 3
0.6375	Remote Similarity	NPD4686	Approved
0.6375	Remote Similarity	NPD4685	Phase 3
0.6374	Remote Similarity	NPD2789	Approved
0.6374	Remote Similarity	NPD6026	Approved
0.6374	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6395	Phase 2
0.6374	Remote Similarity	NPD2326	Approved
0.637	Remote Similarity	NPD4571	Approved
0.637	Remote Similarity	NPD4573	Approved
0.637	Remote Similarity	NPD4572	Approved
0.6369	Remote Similarity	NPD4365	Phase 2
0.6369	Remote Similarity	NPD1405	Approved
0.6358	Remote Similarity	NPD6524	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD5599	Discontinued
0.6353	Remote Similarity	NPD5811	Approved
0.6348	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD6378	Approved
0.6344	Remote Similarity	NPD4499	Approved
0.634	Remote Similarity	NPD31	Approved
0.634	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.634	Remote Similarity	NPD4038	Approved
0.634	Remote Similarity	NPD4033	Approved
0.634	Remote Similarity	NPD3529	Phase 2
0.634	Remote Similarity	NPD32	Approved
0.634	Remote Similarity	NPD4039	Approved
0.634	Remote Similarity	NPD4034	Approved
0.634	Remote Similarity	NPD4122	Approved
0.634	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.634	Remote Similarity	NPD4037	Approved
0.634	Remote Similarity	NPD4035	Approved
0.634	Remote Similarity	NPD4036	Approved
0.6337	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6886	Approved
0.6337	Remote Similarity	NPD6885	Approved
0.6337	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5600	Discontinued
0.6328	Remote Similarity	NPD7474	Suspended
0.6324	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD5578	Approved
0.6323	Remote Similarity	NPD1036	Approved
0.6321	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD3037	Phase 1
0.6316	Remote Similarity	NPD7969	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD1417	Approved
0.6312	Remote Similarity	NPD1419	Approved
0.6312	Remote Similarity	NPD5716	Approved
0.6309	Remote Similarity	NPD4031	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