NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	488.18
Volume:	451.688
LogP:	1.004
LogD:	0.778
LogS:	-4.235
# Rotatable Bonds:	5
TPSA:	141.53
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.381
Synthetic Accessibility Score:	6.803
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.545
MDCK Permeability:	2.1662597646354698e-05
Pgp-inhibitor:	0.053
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.698
Plasma Protein Binding (PPB):	48.60554885864258%
Volume Distribution (VD):	1.007
Pgp-substrate:	50.493385314941406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.134
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.575
CYP3A4-inhibitor:	0.153
CYP3A4-substrate:	0.939

ADMET: Excretion

Clearance (CL):	2.587
Half-life (T1/2):	0.476

ADMET: Toxicity

hERG Blockers:	0.131
Human Hepatotoxicity (H-HT):	0.69
Drug-inuced Liver Injury (DILI):	0.08
AMES Toxicity:	0.922
Rat Oral Acute Toxicity:	0.985
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.101
Carcinogencity:	0.438
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.457

Download Data

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

Natural Product: NPC477395

Natural Product ID:	NPC477395
*Common Name:**	Kopsimaline C
IUPAC Name:	dimethyl (1R,2R,4S,9R,17S,18R,19R,22R)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.11,6.02,4.09,17.010,15.09,22]docosa-10(15),11,13-triene-16,18-dicarboxylate
Synonyms:	Kopsimaline C
Standard InCHIKey:	GXDHEFQHGXMJAL-JXFMMCSMSA-N
Standard InCHI:	InChI=1S/C24H28N2O9/c1-32-12-5-4-11-14(15(12)27)26(20(30)34-3)23-7-6-21(18(28)24(23,31)19(29)33-2)16-13(35-16)10-25-9-8-22(11,23)17(21)25/h4-5,13,16-18,27-28,31H,6-10H2,1-3H3/t13-,16-,17-,18+,21+,22+,23-,24+/m0/s1
SMILES:	COC1=C(C2=C(C=C1)[C@]34CCN5[C@H]3[C@@]6(CC[C@@]4(N2C(=O)OC)[C@@]([C@@H]6O)(C(=O)OC)O)[C@@H]7[C@H](C5)O7)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	24770357
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003755] Aspidofractine 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
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17939738]
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	leaf and stem-bark	Pahang, Malaysia	1996-JUL	PMID[18078327]
NPO19270	Kopsia singapurensis	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	18.2	ug/ml	PMID[18078327]
NPT2	Others	Unspecified		IC50	>	25	ug/ml	PMID[18078327]

☑ 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 NPC477395 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	446
0.1-0.2	1840
0.2-0.3	4911
0.3-0.4	11369
0.4-0.5	12985
0.5-0.6	9833
0.6-0.7	1159
0.7-0.8	135
0.8-0.85	8
0.85-0.9	4
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9543	High Similarity	NPC477393
0.9457	High Similarity	NPC477396
0.9346	High Similarity	NPC471513
0.9171	High Similarity	NPC477397
0.9078	High Similarity	NPC473458
0.8986	High Similarity	NPC477394
0.8843	High Similarity	NPC222046
0.8756	High Similarity	NPC288110
0.8565	High Similarity	NPC470480
0.8546	High Similarity	NPC291173
0.8393	Intermediate Similarity	NPC19175
0.8311	Intermediate Similarity	NPC127996
0.8214	Intermediate Similarity	NPC10653
0.8214	Intermediate Similarity	NPC318525
0.8102	Intermediate Similarity	NPC471512
0.8097	Intermediate Similarity	NPC128476
0.808	Intermediate Similarity	NPC195636
0.8	Intermediate Similarity	NPC161804
0.7974	Intermediate Similarity	NPC476069
0.7902	Intermediate Similarity	NPC159815
0.7885	Intermediate Similarity	NPC77777
0.7876	Intermediate Similarity	NPC234772
0.7872	Intermediate Similarity	NPC160113
0.7872	Intermediate Similarity	NPC476220
0.7835	Intermediate Similarity	NPC231924
0.7824	Intermediate Similarity	NPC221687
0.7812	Intermediate Similarity	NPC269449
0.7793	Intermediate Similarity	NPC195787
0.7793	Intermediate Similarity	NPC246140
0.7743	Intermediate Similarity	NPC470482
0.7743	Intermediate Similarity	NPC470481
0.7741	Intermediate Similarity	NPC476258
0.7741	Intermediate Similarity	NPC304837
0.7706	Intermediate Similarity	NPC473375
0.7706	Intermediate Similarity	NPC97100
0.7689	Intermediate Similarity	NPC154922
0.7686	Intermediate Similarity	NPC126556
0.7672	Intermediate Similarity	NPC148124
0.7665	Intermediate Similarity	NPC119722
0.7658	Intermediate Similarity	NPC1464
0.7629	Intermediate Similarity	NPC99724
0.7617	Intermediate Similarity	NPC248903
0.7613	Intermediate Similarity	NPC151470
0.7613	Intermediate Similarity	NPC201055
0.7613	Intermediate Similarity	NPC64576
0.7613	Intermediate Similarity	NPC254045
0.7603	Intermediate Similarity	NPC113455
0.7588	Intermediate Similarity	NPC10732
0.7582	Intermediate Similarity	NPC120239
0.7574	Intermediate Similarity	NPC26928
0.7568	Intermediate Similarity	NPC127178
0.7511	Intermediate Similarity	NPC470484
0.7489	Intermediate Similarity	NPC67904
0.7459	Intermediate Similarity	NPC469452
0.7455	Intermediate Similarity	NPC471489
0.7455	Intermediate Similarity	NPC470485
0.7434	Intermediate Similarity	NPC87714
0.7432	Intermediate Similarity	NPC66909
0.7426	Intermediate Similarity	NPC285254
0.7411	Intermediate Similarity	NPC474427
0.7411	Intermediate Similarity	NPC138830
0.7404	Intermediate Similarity	NPC46259
0.7404	Intermediate Similarity	NPC76478
0.7399	Intermediate Similarity	NPC17677
0.7398	Intermediate Similarity	NPC329932
0.7388	Intermediate Similarity	NPC469722
0.7377	Intermediate Similarity	NPC469450
0.7364	Intermediate Similarity	NPC470483
0.7357	Intermediate Similarity	NPC475147
0.7336	Intermediate Similarity	NPC301501
0.7331	Intermediate Similarity	NPC7560
0.7322	Intermediate Similarity	NPC13249
0.7317	Intermediate Similarity	NPC469451
0.7304	Intermediate Similarity	NPC475133
0.7296	Intermediate Similarity	NPC189661
0.7295	Intermediate Similarity	NPC131977
0.728	Intermediate Similarity	NPC476436
0.728	Intermediate Similarity	NPC266994
0.7277	Intermediate Similarity	NPC182853
0.7277	Intermediate Similarity	NPC474432
0.7277	Intermediate Similarity	NPC475713
0.7257	Intermediate Similarity	NPC118189
0.7253	Intermediate Similarity	NPC114468
0.7252	Intermediate Similarity	NPC196231
0.7244	Intermediate Similarity	NPC265642
0.7244	Intermediate Similarity	NPC218733
0.7244	Intermediate Similarity	NPC138615
0.7244	Intermediate Similarity	NPC132874
0.7229	Intermediate Similarity	NPC477160
0.7222	Intermediate Similarity	NPC2905
0.7222	Intermediate Similarity	NPC148391
0.722	Intermediate Similarity	NPC74216
0.722	Intermediate Similarity	NPC78284
0.722	Intermediate Similarity	NPC94499
0.7203	Intermediate Similarity	NPC134702
0.7193	Intermediate Similarity	NPC286135
0.7193	Intermediate Similarity	NPC475747
0.719	Intermediate Similarity	NPC223242
0.7173	Intermediate Similarity	NPC219397
0.7168	Intermediate Similarity	NPC293624
0.7155	Intermediate Similarity	NPC71539
0.7155	Intermediate Similarity	NPC251071
0.7155	Intermediate Similarity	NPC250960
0.7143	Intermediate Similarity	NPC11708
0.7131	Intermediate Similarity	NPC476429
0.7131	Intermediate Similarity	NPC139373
0.7123	Intermediate Similarity	NPC99179
0.7116	Intermediate Similarity	NPC260909
0.7104	Intermediate Similarity	NPC474746
0.7104	Intermediate Similarity	NPC475981
0.7094	Intermediate Similarity	NPC237901
0.7094	Intermediate Similarity	NPC195788
0.7093	Intermediate Similarity	NPC23080
0.7093	Intermediate Similarity	NPC193906
0.7085	Intermediate Similarity	NPC22689
0.7085	Intermediate Similarity	NPC474059
0.7085	Intermediate Similarity	NPC105055
0.7059	Intermediate Similarity	NPC87560
0.7049	Intermediate Similarity	NPC470821
0.704	Intermediate Similarity	NPC230098
0.704	Intermediate Similarity	NPC477186
0.7034	Intermediate Similarity	NPC321166
0.7034	Intermediate Similarity	NPC217903
0.7034	Intermediate Similarity	NPC30749
0.7029	Intermediate Similarity	NPC475609
0.7027	Intermediate Similarity	NPC262725
0.7026	Intermediate Similarity	NPC476500
0.7025	Intermediate Similarity	NPC122886
0.7021	Intermediate Similarity	NPC220241
0.7021	Intermediate Similarity	NPC295479
0.7014	Intermediate Similarity	NPC115906
0.7008	Intermediate Similarity	NPC315914
0.7004	Intermediate Similarity	NPC162653
0.7	Intermediate Similarity	NPC232600
0.7	Intermediate Similarity	NPC15919
0.6996	Remote Similarity	NPC212123
0.6996	Remote Similarity	NPC9867
0.6992	Remote Similarity	NPC475316
0.6992	Remote Similarity	NPC305542
0.6992	Remote Similarity	NPC116178
0.6992	Remote Similarity	NPC473486
0.6988	Remote Similarity	NPC151171
0.6987	Remote Similarity	NPC195120
0.6983	Remote Similarity	NPC268077
0.6968	Remote Similarity	NPC474745
0.6968	Remote Similarity	NPC220961
0.6964	Remote Similarity	NPC162694
0.6962	Remote Similarity	NPC268223
0.6955	Remote Similarity	NPC474470
0.6953	Remote Similarity	NPC80472
0.6953	Remote Similarity	NPC189079
0.6951	Remote Similarity	NPC156576
0.6951	Remote Similarity	NPC470631
0.6951	Remote Similarity	NPC35390
0.6951	Remote Similarity	NPC473781
0.6949	Remote Similarity	NPC82541
0.6943	Remote Similarity	NPC124302
0.6943	Remote Similarity	NPC215098
0.6943	Remote Similarity	NPC70290
0.6943	Remote Similarity	NPC73020
0.6943	Remote Similarity	NPC46744
0.6943	Remote Similarity	NPC14622
0.6933	Remote Similarity	NPC237579
0.693	Remote Similarity	NPC33256
0.6929	Remote Similarity	NPC118154
0.6929	Remote Similarity	NPC157983
0.6923	Remote Similarity	NPC474325
0.692	Remote Similarity	NPC21425
0.6914	Remote Similarity	NPC133609
0.6913	Remote Similarity	NPC267414
0.6906	Remote Similarity	NPC52262
0.6906	Remote Similarity	NPC248642
0.6903	Remote Similarity	NPC203628
0.6903	Remote Similarity	NPC25401
0.6903	Remote Similarity	NPC22476
0.6898	Remote Similarity	NPC33507
0.6897	Remote Similarity	NPC202771
0.6897	Remote Similarity	NPC2173
0.6897	Remote Similarity	NPC328700
0.6897	Remote Similarity	NPC119818
0.6897	Remote Similarity	NPC474077
0.6895	Remote Similarity	NPC316292
0.6894	Remote Similarity	NPC207873
0.6894	Remote Similarity	NPC100573
0.6889	Remote Similarity	NPC320088
0.6888	Remote Similarity	NPC37957
0.6883	Remote Similarity	NPC226652
0.6883	Remote Similarity	NPC120671
0.6883	Remote Similarity	NPC314100
0.6883	Remote Similarity	NPC72788
0.6878	Remote Similarity	NPC237044
0.687	Remote Similarity	NPC100863
0.6867	Remote Similarity	NPC207971
0.6861	Remote Similarity	NPC298339
0.6856	Remote Similarity	NPC303214
0.6853	Remote Similarity	NPC469732
0.6849	Remote Similarity	NPC311991
0.6847	Remote Similarity	NPC148693
0.6847	Remote Similarity	NPC294790
0.6847	Remote Similarity	NPC118633

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 NPC477395 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	661
0.2-0.3	1159
0.3-0.4	2573
0.4-0.5	2915
0.5-0.6	1395
0.6-0.7	181
0.7-0.8	28
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
0.7613	Intermediate Similarity	NPD2493	Approved
0.7613	Intermediate Similarity	NPD3452	Approved
0.7613	Intermediate Similarity	NPD3450	Approved
0.7613	Intermediate Similarity	NPD2494	Approved
0.7589	Intermediate Similarity	NPD4582	Approved
0.7589	Intermediate Similarity	NPD4583	Approved
0.7545	Intermediate Similarity	NPD4002	Approved
0.7545	Intermediate Similarity	NPD4004	Approved
0.7458	Intermediate Similarity	NPD6625	Approved
0.7447	Intermediate Similarity	NPD6997	Phase 2
0.7432	Intermediate Similarity	NPD2975	Approved
0.7432	Intermediate Similarity	NPD2974	Approved
0.7432	Intermediate Similarity	NPD2973	Approved
0.7411	Intermediate Similarity	NPD4580	Approved
0.7393	Intermediate Similarity	NPD2899	Discontinued
0.7366	Intermediate Similarity	NPD7048	Phase 3
0.7285	Intermediate Similarity	NPD2490	Approved
0.7285	Intermediate Similarity	NPD2488	Approved
0.7232	Intermediate Similarity	NPD5582	Discontinued
0.7205	Intermediate Similarity	NPD4040	Phase 1
0.7191	Intermediate Similarity	NPD7047	Phase 3
0.7117	Intermediate Similarity	NPD7906	Approved
0.7116	Intermediate Similarity	NPD8459	Approved
0.7116	Intermediate Similarity	NPD8460	Approved
0.7113	Intermediate Similarity	NPD7907	Approved
0.7101	Intermediate Similarity	NPD4111	Phase 1
0.7094	Intermediate Similarity	NPD8466	Approved
0.7094	Intermediate Similarity	NPD8467	Approved
0.7094	Intermediate Similarity	NPD8465	Approved
0.7033	Intermediate Similarity	NPD6723	Discontinued
0.7029	Intermediate Similarity	NPD4665	Approved
0.7014	Intermediate Similarity	NPD2968	Approved
0.7014	Intermediate Similarity	NPD4577	Approved
0.7014	Intermediate Similarity	NPD4578	Approved
0.7014	Intermediate Similarity	NPD2971	Approved
0.6996	Remote Similarity	NPD4663	Approved
0.6996	Remote Similarity	NPD7186	Phase 3
0.6989	Remote Similarity	NPD8425	Approved
0.6989	Remote Similarity	NPD8426	Approved
0.6966	Remote Similarity	NPD8429	Approved
0.6966	Remote Similarity	NPD8428	Approved
0.6966	Remote Similarity	NPD8427	Approved
0.6943	Remote Similarity	NPD4420	Approved
0.6914	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5006	Approved
0.6897	Remote Similarity	NPD5005	Approved
0.6861	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD8461	Discontinued
0.6831	Remote Similarity	NPD7805	Phase 3
0.6807	Remote Similarity	NPD5676	Approved
0.6805	Remote Similarity	NPD8364	Approved
0.6805	Remote Similarity	NPD8363	Approved
0.6802	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD5313	Approved
0.6787	Remote Similarity	NPD5312	Approved
0.6786	Remote Similarity	NPD7310	Approved
0.6786	Remote Similarity	NPD7311	Approved
0.6786	Remote Similarity	NPD7312	Approved
0.6786	Remote Similarity	NPD7313	Approved
0.6783	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7827	Phase 1
0.6769	Remote Similarity	NPD8492	Approved
0.6756	Remote Similarity	NPD7309	Approved
0.6754	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD2491	Approved
0.6752	Remote Similarity	NPD3057	Approved
0.6752	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD3448	Approved
0.6736	Remote Similarity	NPD1945	Phase 1
0.6727	Remote Similarity	NPD2489	Approved
0.6727	Remote Similarity	NPD27	Approved
0.6725	Remote Similarity	NPD7296	Approved
0.6723	Remote Similarity	NPD7497	Discontinued
0.6714	Remote Similarity	NPD8489	Phase 1
0.6712	Remote Similarity	NPD3051	Approved
0.6709	Remote Similarity	NPD7263	Phase 2
0.6692	Remote Similarity	NPD7803	Approved
0.6692	Remote Similarity	NPD7955	Approved
0.6692	Remote Similarity	NPD7956	Approved
0.6682	Remote Similarity	NPD2970	Approved
0.6682	Remote Similarity	NPD2969	Approved
0.6681	Remote Similarity	NPD3533	Approved
0.6681	Remote Similarity	NPD2972	Approved
0.6681	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4859	Phase 1
0.668	Remote Similarity	NPD8367	Approved
0.6667	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4107	Approved
0.6667	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD3437	Discontinued
0.6653	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD4481	Phase 3
0.6639	Remote Similarity	NPD4596	Phase 1
0.6627	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7560	Approved
0.6624	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD3298	Approved
0.6614	Remote Similarity	NPD4846	Phase 2
0.6613	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD4455	Discontinued
0.6611	Remote Similarity	NPD2906	Approved
0.6611	Remote Similarity	NPD2907	Approved
0.6609	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4493	Discontinued
0.6585	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD6716	Phase 1
0.6573	Remote Similarity	NPD3912	Discontinued
0.657	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.657	Remote Similarity	NPD4492	Approved
0.657	Remote Similarity	NPD4494	Approved
0.6568	Remote Similarity	NPD4482	Phase 3
0.6561	Remote Similarity	NPD7922	Phase 1
0.6556	Remote Similarity	NPD5860	Discontinued
0.6555	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD8067	Phase 3
0.6544	Remote Similarity	NPD7684	Approved
0.6544	Remote Similarity	NPD7682	Approved
0.6543	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4082	Approved
0.6541	Remote Similarity	NPD7708	Approved
0.6535	Remote Similarity	NPD6851	Approved
0.6535	Remote Similarity	NPD6853	Approved
0.6513	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6511	Remote Similarity	NPD4668	Phase 2
0.6506	Remote Similarity	NPD7279	Phase 2
0.6506	Remote Similarity	NPD7278	Phase 2
0.6506	Remote Similarity	NPD7820	Phase 3
0.6504	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD3888	Discontinued
0.6498	Remote Similarity	NPD6238	Discontinued
0.6491	Remote Similarity	NPD7280	Phase 3
0.6491	Remote Similarity	NPD7281	Phase 3
0.6488	Remote Similarity	NPD3893	Discontinued
0.6485	Remote Similarity	NPD6644	Discontinued
0.6483	Remote Similarity	NPD6874	Approved
0.6473	Remote Similarity	NPD4022	Approved
0.6473	Remote Similarity	NPD3472	Approved
0.6463	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD8404	Phase 2
0.6461	Remote Similarity	NPD683	Approved
0.6456	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7292	Approved
0.6432	Remote Similarity	NPD6297	Approved
0.6426	Remote Similarity	NPD8153	Approved
0.6426	Remote Similarity	NPD8152	Approved
0.642	Remote Similarity	NPD3372	Discontinued
0.6414	Remote Similarity	NPD5608	Approved
0.6414	Remote Similarity	NPD3297	Approved
0.6414	Remote Similarity	NPD5609	Approved
0.6413	Remote Similarity	NPD6071	Discontinued
0.6411	Remote Similarity	NPD5496	Approved
0.6404	Remote Similarity	NPD7169	Suspended
0.6404	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5938	Phase 3
0.6398	Remote Similarity	NPD4604	Approved
0.6398	Remote Similarity	NPD4605	Approved
0.6395	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD4206	Approved
0.6393	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7224	Discontinued
0.6389	Remote Similarity	NPD7223	Discontinued
0.6387	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD6517	Phase 3
0.6382	Remote Similarity	NPD7559	Phase 2
0.6379	Remote Similarity	NPD3591	Approved
0.6379	Remote Similarity	NPD3592	Approved
0.6378	Remote Similarity	NPD6199	Discontinued
0.6375	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD7293	Approved
0.6371	Remote Similarity	NPD5071	Phase 2
0.636	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD2845	Phase 2
0.6352	Remote Similarity	NPD2843	Phase 2
0.6345	Remote Similarity	NPD7811	Phase 3
0.6345	Remote Similarity	NPD7810	Phase 3
0.6344	Remote Similarity	NPD5600	Discontinued
0.634	Remote Similarity	NPD7262	Phase 1
0.634	Remote Similarity	NPD7125	Discontinued
0.6337	Remote Similarity	NPD7701	Phase 2
0.6331	Remote Similarity	NPD5980	Discovery
0.6325	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.632	Remote Similarity	NPD8053	Approved
0.632	Remote Similarity	NPD8054	Approved
0.6316	Remote Similarity	NPD7479	Phase 2
0.6316	Remote Similarity	NPD7930	Approved
0.6309	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD8016	Phase 3
0.6308	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6494	Phase 2
0.6295	Remote Similarity	NPD6107	Approved
0.629	Remote Similarity	NPD8149	Discontinued
0.6276	Remote Similarity	NPD7565	Approved
0.6271	Remote Similarity	NPD5610	Approved
0.627	Remote Similarity	NPD7300	Phase 3

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