NPASS Compound

Structure

NPC476425 OpenBabel07101718232D 30 35 0 0 1 0 0 0 0 0999 V2000 2.9542 0.7027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6174 -1.6391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5295 3.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3379 -1.4866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0882 0.2027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7659 1.6047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7677 2.3248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1414 1.2462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1450 2.6864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9199 1.3413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1411 1.6119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2222 1.2099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7603 -1.1241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2222 0.7027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5187 1.6078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7829 0.4491 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5205 2.3279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3078 2.0046 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6561 0.7547 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4115 1.9706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9205 0.3908 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.3092 -0.9510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8333 1.3870 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8362 2.5521 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7829 1.4635 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.8857 -1.6089 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2874 -1.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3597 -1.6943 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7777 -0.1242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 13 1 0 0 0 0 3 25 1 0 0 0 0 4 29 1 0 0 0 0 5 14 2 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 15 2 0 0 0 0 9 17 2 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 26 1 0 0 0 0 13 27 2 0 0 0 0 13 30 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 24 1 1 0 0 0 17 25 1 0 0 0 0 18 10 1 6 0 0 0 18 20 1 0 0 0 0 18 26 1 0 0 0 0 19 24 1 6 0 0 0 19 26 1 0 0 0 0 20 23 1 6 0 0 0 20 25 1 0 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 21 30 1 0 0 0 0 22 28 2 0 0 0 0 22 29 1 0 0 0 0 23 11 1 1 0 0 0 24 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.2
Volume:	413.657
LogP:	1.784
LogD:	1.958
LogS:	-3.64
# Rotatable Bonds:	4
TPSA:	59.08
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.553
Synthetic Accessibility Score:	6.597
Fsp3:	0.583
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.048
MDCK Permeability:	3.921911047655158e-05
Pgp-inhibitor:	0.055
Pgp-substrate:	0.609
Human Intestinal Absorption (HIA):	0.935
20% Bioavailability (F20%):	0.914
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.9
Plasma Protein Binding (PPB):	58.869667053222656%
Volume Distribution (VD):	1.997
Pgp-substrate:	42.60054016113281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.108
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.36
CYP2C19-substrate:	0.905
CYP2C9-inhibitor:	0.088
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.67
CYP2D6-substrate:	0.824
CYP3A4-inhibitor:	0.864
CYP3A4-substrate:	0.85

ADMET: Excretion

Clearance (CL):	5.656
Half-life (T1/2):	0.069

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.393
Drug-inuced Liver Injury (DILI):	0.659
AMES Toxicity:	0.079
Rat Oral Acute Toxicity:	0.887
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.42
Carcinogencity:	0.932
Eye Corrosion:	0.007
Eye Irritation:	0.019
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC476425

Natural Product ID:	NPC476425
*Common Name:**	Vincamedine
IUPAC Name:	n.a.
Synonyms:	Vincamedine
Standard InCHIKey:	UBTOXVLVFCOIGT-KFNUSGDOSA-N
Standard InCHI:	InChI=1S/C24H28N2O4/c1-5-14-12-26-18-10-16(14)24(22(28)29-4)19(26)11-23(21(24)30-13(2)27)15-8-6-7-9-17(15)25(3)20(18)23/h5-9,16,18-21H,10-12H2,1-4H3/b14-5+/t16-,18-,19-,20+,21?,23+,24-/m0/s1
SMILES:	CC=C1CN2C3CC1C4(C2CC5(C3N(C6=CC=CC=C65)C)C4OC(=O)C)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL600638
PubChem CID:	46229134
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	=	22.0	%	PMID[512961]
NPT641	Individual Protein	Sodium/glucose cotransporter 2	Homo sapiens	Inhibition	=	47.4	%	PMID[512961]

☑ 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 NPC476425 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	273
0.1-0.2	1229
0.2-0.3	3333
0.3-0.4	18944
0.4-0.5	14534
0.5-0.6	3514
0.6-0.7	689
0.7-0.8	162
0.8-0.85	13
0.85-0.9	1
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9623	High Similarity	NPC476441
0.9563	High Similarity	NPC476326
0.9268	High Similarity	NPC476428
0.9161	High Similarity	NPC478076
0.8439	Intermediate Similarity	NPC472209
0.8121	Intermediate Similarity	NPC29285
0.8107	Intermediate Similarity	NPC472115
0.8107	Intermediate Similarity	NPC472114
0.8059	Intermediate Similarity	NPC469462
0.8023	Intermediate Similarity	NPC469460
0.7964	Intermediate Similarity	NPC113946
0.7941	Intermediate Similarity	NPC472106
0.7917	Intermediate Similarity	NPC469461
0.787	Intermediate Similarity	NPC225319
0.7824	Intermediate Similarity	NPC176983
0.775	Intermediate Similarity	NPC476436
0.7738	Intermediate Similarity	NPC161827
0.7719	Intermediate Similarity	NPC282339
0.7719	Intermediate Similarity	NPC99632
0.7714	Intermediate Similarity	NPC139085
0.7714	Intermediate Similarity	NPC214626
0.7714	Intermediate Similarity	NPC251212
0.766	Intermediate Similarity	NPC475489
0.7647	Intermediate Similarity	NPC153694
0.7647	Intermediate Similarity	NPC211525
0.7633	Intermediate Similarity	NPC473297
0.763	Intermediate Similarity	NPC52059
0.763	Intermediate Similarity	NPC470069
0.7624	Intermediate Similarity	NPC52262
0.7616	Intermediate Similarity	NPC286871
0.7616	Intermediate Similarity	NPC472101
0.7616	Intermediate Similarity	NPC472120
0.7602	Intermediate Similarity	NPC148468
0.7602	Intermediate Similarity	NPC97380
0.7602	Intermediate Similarity	NPC263709
0.7602	Intermediate Similarity	NPC63210
0.7602	Intermediate Similarity	NPC243673
0.7602	Intermediate Similarity	NPC310403
0.7571	Intermediate Similarity	NPC13367
0.7561	Intermediate Similarity	NPC476429
0.7514	Intermediate Similarity	NPC210415
0.7514	Intermediate Similarity	NPC181138
0.7514	Intermediate Similarity	NPC21752
0.7514	Intermediate Similarity	NPC276993
0.7514	Intermediate Similarity	NPC293255
0.7514	Intermediate Similarity	NPC298851
0.75	Intermediate Similarity	NPC90967
0.7487	Intermediate Similarity	NPC34717
0.7486	Intermediate Similarity	NPC260075
0.746	Intermediate Similarity	NPC52557
0.7459	Intermediate Similarity	NPC473298
0.7459	Intermediate Similarity	NPC22689
0.7459	Intermediate Similarity	NPC105055
0.7457	Intermediate Similarity	NPC143457
0.7457	Intermediate Similarity	NPC474058
0.7446	Intermediate Similarity	NPC181928
0.7446	Intermediate Similarity	NPC21425
0.7432	Intermediate Similarity	NPC472107
0.7432	Intermediate Similarity	NPC79062
0.743	Intermediate Similarity	NPC264482
0.743	Intermediate Similarity	NPC203202
0.7418	Intermediate Similarity	NPC477159
0.7416	Intermediate Similarity	NPC96901
0.7399	Intermediate Similarity	NPC193410
0.7394	Intermediate Similarity	NPC221687
0.7389	Intermediate Similarity	NPC186669
0.7386	Intermediate Similarity	NPC214960
0.7386	Intermediate Similarity	NPC279527
0.7377	Intermediate Similarity	NPC472119
0.7356	Intermediate Similarity	NPC248117
0.7351	Intermediate Similarity	NPC14994
0.7348	Intermediate Similarity	NPC6974
0.7345	Intermediate Similarity	NPC167724
0.7345	Intermediate Similarity	NPC223595
0.7345	Intermediate Similarity	NPC224970
0.7341	Intermediate Similarity	NPC61013
0.7322	Intermediate Similarity	NPC159963
0.7316	Intermediate Similarity	NPC162440
0.7316	Intermediate Similarity	NPC475559
0.7314	Intermediate Similarity	NPC472117
0.7297	Intermediate Similarity	NPC282092
0.7263	Intermediate Similarity	NPC97100
0.7263	Intermediate Similarity	NPC473375
0.7257	Intermediate Similarity	NPC309531
0.7257	Intermediate Similarity	NPC472102
0.7253	Intermediate Similarity	NPC218594
0.7253	Intermediate Similarity	NPC99043
0.7234	Intermediate Similarity	NPC25401
0.7222	Intermediate Similarity	NPC285622
0.7219	Intermediate Similarity	NPC472100
0.7216	Intermediate Similarity	NPC293458
0.7216	Intermediate Similarity	NPC472121
0.7207	Intermediate Similarity	NPC472118
0.7202	Intermediate Similarity	NPC138830
0.72	Intermediate Similarity	NPC36495
0.7189	Intermediate Similarity	NPC97584
0.7175	Intermediate Similarity	NPC313757
0.7165	Intermediate Similarity	NPC471512
0.7159	Intermediate Similarity	NPC201424
0.7143	Intermediate Similarity	NPC123241
0.7143	Intermediate Similarity	NPC472097
0.7135	Intermediate Similarity	NPC143533
0.7135	Intermediate Similarity	NPC472104
0.7135	Intermediate Similarity	NPC302548
0.7119	Intermediate Similarity	NPC85651
0.7113	Intermediate Similarity	NPC67904
0.7105	Intermediate Similarity	NPC473004
0.7097	Intermediate Similarity	NPC245741
0.7088	Intermediate Similarity	NPC329338
0.7088	Intermediate Similarity	NPC469726
0.7081	Intermediate Similarity	NPC475962
0.7074	Intermediate Similarity	NPC472323
0.7056	Intermediate Similarity	NPC329833
0.7041	Intermediate Similarity	NPC162730
0.7039	Intermediate Similarity	NPC471124
0.7037	Intermediate Similarity	NPC284706
0.7037	Intermediate Similarity	NPC175474
0.7031	Intermediate Similarity	NPC57994
0.7031	Intermediate Similarity	NPC289299
0.7026	Intermediate Similarity	NPC195461
0.7026	Intermediate Similarity	NPC49196
0.7026	Intermediate Similarity	NPC81654
0.7026	Intermediate Similarity	NPC79129
0.7026	Intermediate Similarity	NPC313985
0.7026	Intermediate Similarity	NPC249150
0.7021	Intermediate Similarity	NPC66210
0.7006	Intermediate Similarity	NPC471122
0.7005	Intermediate Similarity	NPC258480
0.7005	Intermediate Similarity	NPC477179
0.7	Intermediate Similarity	NPC278887
0.7	Intermediate Similarity	NPC473569
0.6995	Remote Similarity	NPC245916
0.6988	Remote Similarity	NPC471123
0.6973	Remote Similarity	NPC321211
0.697	Remote Similarity	NPC477178
0.697	Remote Similarity	NPC477180
0.697	Remote Similarity	NPC254850
0.697	Remote Similarity	NPC477181
0.6954	Remote Similarity	NPC474116
0.695	Remote Similarity	NPC471945
0.695	Remote Similarity	NPC471950
0.6943	Remote Similarity	NPC230313
0.6935	Remote Similarity	NPC477173
0.6935	Remote Similarity	NPC470490
0.6935	Remote Similarity	NPC15840
0.6935	Remote Similarity	NPC477174
0.6931	Remote Similarity	NPC82541
0.6927	Remote Similarity	NPC55493
0.6923	Remote Similarity	NPC50503
0.6923	Remote Similarity	NPC469915
0.6915	Remote Similarity	NPC471946
0.6915	Remote Similarity	NPC471951
0.6907	Remote Similarity	NPC472116
0.69	Remote Similarity	NPC470488
0.6881	Remote Similarity	NPC475359
0.6881	Remote Similarity	NPC191817
0.6879	Remote Similarity	NPC212799
0.6878	Remote Similarity	NPC259626
0.6878	Remote Similarity	NPC234772
0.6878	Remote Similarity	NPC473007
0.6866	Remote Similarity	NPC475259
0.6857	Remote Similarity	NPC243756
0.6853	Remote Similarity	NPC214428
0.6851	Remote Similarity	NPC475420
0.685	Remote Similarity	NPC277350
0.6845	Remote Similarity	NPC11149
0.6845	Remote Similarity	NPC281104
0.6839	Remote Similarity	NPC472113
0.6825	Remote Similarity	NPC2933
0.6823	Remote Similarity	NPC472112
0.6823	Remote Similarity	NPC473008
0.6814	Remote Similarity	NPC159815
0.6814	Remote Similarity	NPC127996
0.6813	Remote Similarity	NPC213126
0.6813	Remote Similarity	NPC169485
0.6813	Remote Similarity	NPC84281
0.6813	Remote Similarity	NPC317474
0.6813	Remote Similarity	NPC291027
0.6805	Remote Similarity	NPC469560
0.6802	Remote Similarity	NPC472103
0.68	Remote Similarity	NPC473329
0.6789	Remote Similarity	NPC322621
0.6784	Remote Similarity	NPC473005
0.6784	Remote Similarity	NPC471436
0.678	Remote Similarity	NPC473006
0.6779	Remote Similarity	NPC288110
0.6778	Remote Similarity	NPC255229
0.6778	Remote Similarity	NPC81229
0.6778	Remote Similarity	NPC315368
0.6776	Remote Similarity	NPC473781
0.6776	Remote Similarity	NPC35390
0.6776	Remote Similarity	NPC470631
0.6774	Remote Similarity	NPC129624
0.6774	Remote Similarity	NPC24594
0.6774	Remote Similarity	NPC472122
0.6772	Remote Similarity	NPC256288
0.6771	Remote Similarity	NPC63199
0.6771	Remote Similarity	NPC102338
0.6771	Remote Similarity	NPC111602
0.6771	Remote Similarity	NPC196251

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 NPC476425 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	537
0.2-0.3	716
0.3-0.4	1754
0.4-0.5	3994
0.5-0.6	1800
0.6-0.7	178
0.7-0.8	2
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8447	Intermediate Similarity	NPD4121	Phase 3
0.8447	Intermediate Similarity	NPD4120	Approved
0.8395	Intermediate Similarity	NPD5742	Approved
0.8395	Intermediate Similarity	NPD5741	Approved
0.8395	Intermediate Similarity	NPD5743	Approved
0.7073	Intermediate Similarity	NPD5185	Approved
0.7073	Intermediate Similarity	NPD5184	Approved
0.7073	Intermediate Similarity	NPD5182	Approved
0.7052	Intermediate Similarity	NPD7606	Phase 3
0.7031	Intermediate Similarity	NPD4602	Approved
0.7026	Intermediate Similarity	NPD4601	Approved
0.7026	Intermediate Similarity	NPD4600	Approved
0.7	Intermediate Similarity	NPD7487	Discontinued
0.6949	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7599	Phase 2
0.6879	Remote Similarity	NPD7478	Approved
0.6872	Remote Similarity	NPD7600	Phase 2
0.6845	Remote Similarity	NPD2569	Approved
0.6845	Remote Similarity	NPD2567	Approved
0.6839	Remote Similarity	NPD4682	Phase 2
0.6813	Remote Similarity	NPD2608	Approved
0.6813	Remote Similarity	NPD2609	Approved
0.6813	Remote Similarity	NPD4215	Approved
0.6813	Remote Similarity	NPD2612	Approved
0.6813	Remote Similarity	NPD4216	Approved
0.6813	Remote Similarity	NPD3132	Approved
0.6813	Remote Similarity	NPD2610	Approved
0.6813	Remote Similarity	NPD3131	Approved
0.6813	Remote Similarity	NPD4217	Approved
0.6813	Remote Similarity	NPD4218	Approved
0.6813	Remote Similarity	NPD2611	Approved
0.6811	Remote Similarity	NPD3423	Phase 2
0.6811	Remote Similarity	NPD3422	Phase 3
0.6772	Remote Similarity	NPD2994	Approved
0.6768	Remote Similarity	NPD4501	Approved
0.6768	Remote Similarity	NPD4500	Approved
0.6736	Remote Similarity	NPD4499	Approved
0.6717	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2115	Approved
0.6709	Remote Similarity	NPD2117	Pre-registration
0.6709	Remote Similarity	NPD2116	Approved
0.6708	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6805	Discontinued
0.6667	Remote Similarity	NPD5997	Discontinued
0.6667	Remote Similarity	NPD3377	Discontinued
0.6667	Remote Similarity	NPD5931	Phase 3
0.6667	Remote Similarity	NPD5932	Phase 3
0.6667	Remote Similarity	NPD5933	Phase 3
0.6648	Remote Similarity	NPD5941	Approved
0.6648	Remote Similarity	NPD5942	Approved
0.6647	Remote Similarity	NPD2670	Approved
0.6646	Remote Similarity	NPD2946	Phase 2
0.6632	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD2613	Approved
0.6625	Remote Similarity	NPD3031	Approved
0.6625	Remote Similarity	NPD3032	Approved
0.6625	Remote Similarity	NPD3030	Approved
0.6593	Remote Similarity	NPD2506	Approved
0.6585	Remote Similarity	NPD4520	Approved
0.6571	Remote Similarity	NPD7295	Approved
0.6559	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD3625	Discontinued
0.651	Remote Similarity	NPD7962	Phase 2
0.651	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3088	Approved
0.6509	Remote Similarity	NPD3614	Approved
0.6509	Remote Similarity	NPD3090	Approved
0.6509	Remote Similarity	NPD3087	Approved
0.6509	Remote Similarity	NPD2573	Approved
0.6509	Remote Similarity	NPD2566	Approved
0.6509	Remote Similarity	NPD3616	Approved
0.6509	Remote Similarity	NPD3615	Approved
0.6509	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3089	Approved
0.6509	Remote Similarity	NPD2570	Approved
0.6509	Remote Similarity	NPD4746	Phase 3
0.6509	Remote Similarity	NPD2574	Discontinued
0.6509	Remote Similarity	NPD2571	Approved
0.6509	Remote Similarity	NPD4745	Approved
0.6497	Remote Similarity	NPD2607	Approved
0.6492	Remote Similarity	NPD4330	Approved
0.6492	Remote Similarity	NPD6878	Phase 2
0.6492	Remote Similarity	NPD4329	Approved
0.6492	Remote Similarity	NPD6879	Phase 2
0.6457	Remote Similarity	NPD2820	Phase 3
0.6457	Remote Similarity	NPD7082	Approved
0.645	Remote Similarity	NPD3828	Approved
0.6448	Remote Similarity	NPD2427	Approved
0.6441	Remote Similarity	NPD6416	Phase 2
0.6436	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD4684	Phase 3
0.6433	Remote Similarity	NPD4685	Phase 3
0.6433	Remote Similarity	NPD4686	Approved
0.6422	Remote Similarity	NPD7205	Discontinued
0.642	Remote Similarity	NPD7259	Approved
0.6418	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD2037	Approved
0.6416	Remote Similarity	NPD3170	Approved
0.6412	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD1802	Approved
0.6404	Remote Similarity	NPD6238	Discontinued
0.6404	Remote Similarity	NPD1801	Approved
0.64	Remote Similarity	NPD6566	Discontinued
0.64	Remote Similarity	NPD2365	Approved
0.6387	Remote Similarity	NPD3792	Approved
0.6387	Remote Similarity	NPD5313	Approved
0.6387	Remote Similarity	NPD5312	Approved
0.6373	Remote Similarity	NPD3470	Approved
0.6373	Remote Similarity	NPD3471	Approved
0.6369	Remote Similarity	NPD7528	Approved
0.6364	Remote Similarity	NPD5024	Approved
0.6364	Remote Similarity	NPD5504	Discontinued
0.6359	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD2432	Approved
0.6349	Remote Similarity	NPD2431	Approved
0.6344	Remote Similarity	NPD7734	Approved
0.6341	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.634	Remote Similarity	NPD8281	Discontinued
0.6339	Remote Similarity	NPD7105	Phase 1
0.6337	Remote Similarity	NPD53	Approved
0.6337	Remote Similarity	NPD7778	Approved
0.6337	Remote Similarity	NPD4397	Phase 1
0.6337	Remote Similarity	NPD7777	Approved
0.6335	Remote Similarity	NPD4576	Approved
0.6335	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD6069	Approved
0.6335	Remote Similarity	NPD4574	Approved
0.6335	Remote Similarity	NPD6070	Approved
0.6331	Remote Similarity	NPD4365	Phase 2
0.633	Remote Similarity	NPD6457	Approved
0.633	Remote Similarity	NPD2454	Approved
0.633	Remote Similarity	NPD2455	Approved
0.6328	Remote Similarity	NPD5918	Discontinued
0.6324	Remote Similarity	NPD7275	Approved
0.6322	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD3393	Approved
0.6321	Remote Similarity	NPD3389	Approved
0.6321	Remote Similarity	NPD3394	Approved
0.6312	Remote Similarity	NPD5629	Discontinued
0.6312	Remote Similarity	NPD4766	Approved
0.631	Remote Similarity	NPD5993	Phase 1
0.631	Remote Similarity	NPD7036	Phase 3
0.631	Remote Similarity	NPD7035	Approved
0.631	Remote Similarity	NPD5430	Discontinued
0.6306	Remote Similarity	NPD1752	Approved
0.6306	Remote Similarity	NPD1756	Approved
0.6301	Remote Similarity	NPD5725	Approved
0.6298	Remote Similarity	NPD8027	Approved
0.6283	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5466	Approved
0.628	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.627	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD3782	Discontinued
0.6263	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4334	Discontinued
0.6257	Remote Similarity	NPD8270	Approved
0.625	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1663	Discontinued
0.6243	Remote Similarity	NPD7126	Discontinued
0.6243	Remote Similarity	NPD2404	Discontinued
0.6243	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD2387	Approved
0.6236	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD7168	Phase 3
0.6223	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.622	Remote Similarity	NPD2907	Approved
0.622	Remote Similarity	NPD2906	Approved
0.6218	Remote Similarity	NPD5600	Discontinued
0.6216	Remote Similarity	NPD8630	Approved
0.6209	Remote Similarity	NPD7595	Discontinued
0.6207	Remote Similarity	NPD6073	Approved
0.6207	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5003	Discontinued
0.6205	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD4178	Approved
0.6205	Remote Similarity	NPD4176	Approved
0.6205	Remote Similarity	NPD7437	Approved
0.6205	Remote Similarity	NPD7436	Approved
0.6201	Remote Similarity	NPD6017	Discontinued
0.6199	Remote Similarity	NPD6489	Phase 3
0.6193	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD4644	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD2948	Discontinued
0.6171	Remote Similarity	NPD6358	Phase 2
0.617	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD1360	Approved
0.6168	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4041	Approved
0.6166	Remote Similarity	NPD3978	Clinical (unspecified phase)

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