NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	680.1
Volume:	599.475
LogP:	3.757
LogD:	2.281
LogS:	-4.574
# Rotatable Bonds:	1
TPSA:	125.53
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	12
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.385
Synthetic Accessibility Score:	7.8
Fsp3:	0.467
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.543
MDCK Permeability:	1.681478534010239e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.211
Human Intestinal Absorption (HIA):	0.84
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118
Plasma Protein Binding (PPB):	81.58556365966797%
Volume Distribution (VD):	1.277
Pgp-substrate:	8.597832679748535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.139
CYP2C19-inhibitor:	0.975
CYP2C19-substrate:	0.955
CYP2C9-inhibitor:	0.984
CYP2C9-substrate:	0.146
CYP2D6-inhibitor:	0.608
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.966
CYP3A4-substrate:	0.99

ADMET: Excretion

Clearance (CL):	8.223
Half-life (T1/2):	0.027

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.419
Drug-inuced Liver Injury (DILI):	0.987
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.827
Maximum Recommended Daily Dose:	0.724
Skin Sensitization:	0.916
Carcinogencity:	0.283
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.01

Download Data

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

Natural Product: NPC477179

Natural Product ID:	NPC477179
*Common Name:**	11'-deoxyverticillin A
IUPAC Name:	(1S,2S,3S,11R,14R)-3-[(1S,3R,11R,14S)-14,18-dimethyl-13,17-dioxo-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-trien-3-yl]-2-hydroxy-14,18-dimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-triene-13,17-dione
Synonyms:	11'-Deoxyverticillin A
Standard InCHIKey:	IMORFARNICQOLW-GIEXXVQOSA-N
Standard InCHI:	InChI=1S/C30H28N6O5S4/c1-25-21(38)35-19-27(14-9-5-7-11-16(14)31-19,13-28(35,44-42-25)23(40)33(25)3)29-15-10-6-8-12-17(15)32-20(29)36-22(39)26(2)34(4)24(41)30(36,18(29)37)45-43-26/h5-12,18-20,31-32,37H,13H2,1-4H3/t18-,19+,20+,25-,26+,27-,28-,29+,30-/m0/s1
SMILES:	C[C@]12C(=O)N3[C@@H]4[C@](C[C@@]3(C(=O)N1C)SS2)(C5=CC=CC=C5N4)[C@]67[C@@H]([C@]89C(=O)N([C@@](C(=O)N8[C@H]6NC1=CC=CC=C71)(SS9)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44584290
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001733] Pyrroloindoles

*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
NPO33665	Gliocladium roseum	Species		Eukaryota	isolated from submerged wood, collected from fresh water	Yunnan Province, China	n.a.	PMID[16252916]

☑ 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
ED50	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT530	Organism	Caenorhabditis elegans	Caenorhabditis elegans	ED50	=	10	ug/ml	PMID[16252916]
NPT1272	Organism	Panagrellus redivivus	Panagrellus redivivus	ED50	=	40	ug/ml	PMID[16252916]
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	ED50	>	400	ug/ml	PMID[16252916]

☑ 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 NPC477179 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	299
0.1-0.2	1540
0.2-0.3	7204
0.3-0.4	24248
0.4-0.5	6369
0.5-0.6	2456
0.6-0.7	493
0.7-0.8	62
0.8-0.85	5
0.85-0.9	1
0.9-0.95	8
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9945	High Similarity	NPC254850
0.9945	High Similarity	NPC477178
0.9945	High Similarity	NPC477181
0.9945	High Similarity	NPC477180
0.989	High Similarity	NPC470490
0.9783	High Similarity	NPC475259
0.9783	High Similarity	NPC471950
0.9783	High Similarity	NPC471945
0.9677	High Similarity	NPC191817
0.9677	High Similarity	NPC475359
0.9674	High Similarity	NPC477174
0.9674	High Similarity	NPC477173
0.9622	High Similarity	NPC470488
0.9519	High Similarity	NPC471946
0.9519	High Similarity	NPC471951
0.9333	High Similarity	NPC128582
0.9259	High Similarity	NPC470491
0.9	High Similarity	NPC470489
0.8028	Intermediate Similarity	NPC475859
0.8028	Intermediate Similarity	NPC475969
0.7981	Intermediate Similarity	NPC477175
0.7981	Intermediate Similarity	NPC470730
0.7914	Intermediate Similarity	NPC242269
0.7907	Intermediate Similarity	NPC165743
0.7814	Intermediate Similarity	NPC276085
0.7778	Intermediate Similarity	NPC474877
0.7778	Intermediate Similarity	NPC477177
0.7772	Intermediate Similarity	NPC471436
0.7732	Intermediate Similarity	NPC307396
0.7731	Intermediate Similarity	NPC477176
0.7731	Intermediate Similarity	NPC470729
0.7716	Intermediate Similarity	NPC276430
0.7706	Intermediate Similarity	NPC63279
0.7671	Intermediate Similarity	NPC297642
0.7617	Intermediate Similarity	NPC312942
0.7617	Intermediate Similarity	NPC327095
0.7553	Intermediate Similarity	NPC471124
0.7551	Intermediate Similarity	NPC259626
0.75	Intermediate Similarity	NPC2933
0.7473	Intermediate Similarity	NPC222029
0.7449	Intermediate Similarity	NPC256288
0.7448	Intermediate Similarity	NPC285622
0.7433	Intermediate Similarity	NPC471122
0.7419	Intermediate Similarity	NPC40455
0.7418	Intermediate Similarity	NPC470731
0.7337	Intermediate Similarity	NPC473615
0.7302	Intermediate Similarity	NPC472102
0.7302	Intermediate Similarity	NPC309531
0.73	Intermediate Similarity	NPC229484
0.7285	Intermediate Similarity	NPC297862
0.7264	Intermediate Similarity	NPC292675
0.7211	Intermediate Similarity	NPC68650
0.7194	Intermediate Similarity	NPC476441
0.719	Intermediate Similarity	NPC329833
0.7188	Intermediate Similarity	NPC472106
0.7186	Intermediate Similarity	NPC477159
0.7184	Intermediate Similarity	NPC162440
0.7182	Intermediate Similarity	NPC470301
0.7176	Intermediate Similarity	NPC470732
0.7149	Intermediate Similarity	NPC19170
0.7083	Intermediate Similarity	NPC286871
0.7083	Intermediate Similarity	NPC472120
0.7083	Intermediate Similarity	NPC472101
0.7083	Intermediate Similarity	NPC176983
0.7053	Intermediate Similarity	NPC470787
0.7053	Intermediate Similarity	NPC472540
0.7053	Intermediate Similarity	NPC472539
0.7033	Intermediate Similarity	NPC106118
0.7027	Intermediate Similarity	NPC476817
0.7021	Intermediate Similarity	NPC66936
0.7019	Intermediate Similarity	NPC472542
0.7019	Intermediate Similarity	NPC471199
0.7019	Intermediate Similarity	NPC90967
0.7019	Intermediate Similarity	NPC472541
0.701	Intermediate Similarity	NPC284706
0.7005	Intermediate Similarity	NPC471663
0.7005	Intermediate Similarity	NPC476425
0.6995	Remote Similarity	NPC225400
0.699	Remote Similarity	NPC472118
0.6974	Remote Similarity	NPC472115
0.6974	Remote Similarity	NPC472114
0.697	Remote Similarity	NPC470548
0.6968	Remote Similarity	NPC272174
0.6965	Remote Similarity	NPC476428
0.6963	Remote Similarity	NPC472538
0.6963	Remote Similarity	NPC470786
0.6963	Remote Similarity	NPC471155
0.693	Remote Similarity	NPC270241
0.6919	Remote Similarity	NPC473880
0.6915	Remote Similarity	NPC166169
0.6907	Remote Similarity	NPC472117
0.6893	Remote Similarity	NPC22689
0.6893	Remote Similarity	NPC105055
0.6888	Remote Similarity	NPC214960
0.6888	Remote Similarity	NPC279527
0.6884	Remote Similarity	NPC475097
0.6875	Remote Similarity	NPC29285
0.6868	Remote Similarity	NPC471123
0.6866	Remote Similarity	NPC475094
0.6861	Remote Similarity	NPC474896
0.6852	Remote Similarity	NPC285192
0.6839	Remote Similarity	NPC113946
0.6834	Remote Similarity	NPC473743
0.6834	Remote Similarity	NPC177261
0.6834	Remote Similarity	NPC139085
0.6834	Remote Similarity	NPC251212
0.6834	Remote Similarity	NPC214626
0.6833	Remote Similarity	NPC471197
0.683	Remote Similarity	NPC31097
0.683	Remote Similarity	NPC253987
0.6825	Remote Similarity	NPC109787
0.6807	Remote Similarity	NPC14812
0.6802	Remote Similarity	NPC471198
0.678	Remote Similarity	NPC476095
0.6773	Remote Similarity	NPC473006
0.6762	Remote Similarity	NPC34717
0.6761	Remote Similarity	NPC475489
0.6751	Remote Similarity	NPC475420
0.6733	Remote Similarity	NPC476326
0.6731	Remote Similarity	NPC473298
0.6715	Remote Similarity	NPC181928
0.6703	Remote Similarity	NPC469560
0.6702	Remote Similarity	NPC473329
0.67	Remote Similarity	NPC355
0.6699	Remote Similarity	NPC52262
0.6696	Remote Similarity	NPC219397
0.6684	Remote Similarity	NPC478076
0.6682	Remote Similarity	NPC221687
0.6667	Remote Similarity	NPC223791
0.6667	Remote Similarity	NPC301501
0.6667	Remote Similarity	NPC107077
0.6667	Remote Similarity	NPC286994
0.6667	Remote Similarity	NPC295548
0.6652	Remote Similarity	NPC248601
0.665	Remote Similarity	NPC302235
0.6632	Remote Similarity	NPC264589
0.6618	Remote Similarity	NPC99043
0.6618	Remote Similarity	NPC218594
0.6615	Remote Similarity	NPC318086
0.6611	Remote Similarity	NPC145754
0.6591	Remote Similarity	NPC162860
0.6582	Remote Similarity	NPC469898
0.6582	Remote Similarity	NPC469452
0.658	Remote Similarity	NPC223242
0.6573	Remote Similarity	NPC97100
0.6573	Remote Similarity	NPC473375
0.6569	Remote Similarity	NPC260075
0.6568	Remote Similarity	NPC469450
0.6566	Remote Similarity	NPC282339
0.6566	Remote Similarity	NPC85651
0.6566	Remote Similarity	NPC99632
0.6566	Remote Similarity	NPC472121
0.6556	Remote Similarity	NPC252794
0.655	Remote Similarity	NPC122886
0.6548	Remote Similarity	NPC473003
0.6548	Remote Similarity	NPC36495
0.6533	Remote Similarity	NPC15384
0.6533	Remote Similarity	NPC244425
0.6527	Remote Similarity	NPC329932
0.6524	Remote Similarity	NPC139373
0.6517	Remote Similarity	NPC63047
0.6517	Remote Similarity	NPC475248
0.6515	Remote Similarity	NPC225319
0.6515	Remote Similarity	NPC315368
0.6513	Remote Similarity	NPC469451
0.6512	Remote Similarity	NPC52557
0.6511	Remote Similarity	NPC478028
0.65	Remote Similarity	NPC54420
0.6498	Remote Similarity	NPC471512
0.649	Remote Similarity	NPC97584
0.6483	Remote Similarity	NPC131977
0.6468	Remote Similarity	NPC473005
0.6465	Remote Similarity	NPC469902
0.6462	Remote Similarity	NPC473002
0.6456	Remote Similarity	NPC478029
0.6452	Remote Similarity	NPC138830
0.645	Remote Similarity	NPC328270
0.645	Remote Similarity	NPC313757
0.6447	Remote Similarity	NPC324850
0.6442	Remote Similarity	NPC159963
0.6441	Remote Similarity	NPC477160
0.644	Remote Similarity	NPC472103
0.6439	Remote Similarity	NPC469900
0.6439	Remote Similarity	NPC129624
0.6436	Remote Similarity	NPC473000
0.6432	Remote Similarity	NPC477714
0.6429	Remote Similarity	NPC478077
0.6415	Remote Similarity	NPC473569
0.6414	Remote Similarity	NPC61013
0.6414	Remote Similarity	NPC104345
0.6414	Remote Similarity	NPC469428
0.641	Remote Similarity	NPC475763
0.64	Remote Similarity	NPC469741
0.6398	Remote Similarity	NPC14994
0.6398	Remote Similarity	NPC285841
0.6388	Remote Similarity	NPC477715
0.6387	Remote Similarity	NPC470784
0.6382	Remote Similarity	NPC193410
0.6377	Remote Similarity	NPC6974
0.6376	Remote Similarity	NPC67904

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 NPC477179 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	509
0.2-0.3	681
0.3-0.4	2098
0.4-0.5	3913
0.5-0.6	1690
0.6-0.7	88
0.7-0.8	6
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
0.7716	Intermediate Similarity	NPD8240	Discontinued
0.6863	Remote Similarity	NPD6557	Phase 2
0.6859	Remote Similarity	NPD4121	Phase 3
0.6859	Remote Similarity	NPD4120	Approved
0.6832	Remote Similarity	NPD6879	Phase 2
0.6832	Remote Similarity	NPD6878	Phase 2
0.6823	Remote Similarity	NPD5743	Approved
0.6823	Remote Similarity	NPD5742	Approved
0.6823	Remote Similarity	NPD5741	Approved
0.6753	Remote Similarity	NPD8630	Approved
0.672	Remote Similarity	NPD3625	Discontinued
0.6649	Remote Similarity	NPD5941	Approved
0.6649	Remote Similarity	NPD5024	Approved
0.6649	Remote Similarity	NPD5942	Approved
0.6635	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD5775	Approved
0.6537	Remote Similarity	NPD5774	Approved
0.6532	Remote Similarity	NPD7595	Discontinued
0.65	Remote Similarity	NPD8322	Phase 2
0.6497	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD7599	Phase 2
0.6418	Remote Similarity	NPD4976	Discontinued
0.6409	Remote Similarity	NPD8114	Approved
0.6409	Remote Similarity	NPD8115	Approved
0.6392	Remote Similarity	NPD4682	Phase 2
0.6372	Remote Similarity	NPD4602	Approved
0.6368	Remote Similarity	NPD3790	Phase 2
0.6368	Remote Similarity	NPD7824	Approved
0.6364	Remote Similarity	NPD7105	Phase 1
0.6356	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD7951	Approved
0.6356	Remote Similarity	NPD7789	Approved
0.6356	Remote Similarity	NPD7953	Approved
0.6356	Remote Similarity	NPD7950	Approved
0.6356	Remote Similarity	NPD7952	Approved
0.6356	Remote Similarity	NPD7791	Approved
0.6356	Remote Similarity	NPD7790	Approved
0.635	Remote Similarity	NPD7600	Phase 2
0.6341	Remote Similarity	NPD5997	Discontinued
0.6308	Remote Similarity	NPD4432	Discontinued
0.6301	Remote Similarity	NPD4601	Approved
0.6301	Remote Similarity	NPD4600	Approved
0.6296	Remote Similarity	NPD6358	Phase 2
0.6294	Remote Similarity	NPD8401	Approved
0.6294	Remote Similarity	NPD8402	Approved
0.6294	Remote Similarity	NPD8400	Approved
0.6293	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD7731	Approved
0.6282	Remote Similarity	NPD7730	Approved
0.6269	Remote Similarity	NPD5918	Discontinued
0.6267	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD7271	Approved
0.625	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD4514	Approved
0.6218	Remote Similarity	NPD6301	Phase 2
0.6211	Remote Similarity	NPD6294	Approved
0.6211	Remote Similarity	NPD6295	Approved
0.621	Remote Similarity	NPD5856	Discontinued
0.6205	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7569	Approved
0.6204	Remote Similarity	NPD7570	Approved
0.6203	Remote Similarity	NPD5581	Approved
0.6199	Remote Similarity	NPD7817	Phase 1
0.6195	Remote Similarity	NPD7890	Discontinued
0.6193	Remote Similarity	NPD5748	Phase 2
0.619	Remote Similarity	NPD3989	Phase 3
0.6186	Remote Similarity	NPD7781	Approved
0.6186	Remote Similarity	NPD7780	Approved
0.617	Remote Similarity	NPD8289	Discontinued
0.6169	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD7968	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD3990	Phase 3
0.6157	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD5076	Approved
0.6157	Remote Similarity	NPD5077	Approved
0.6157	Remote Similarity	NPD7970	Approved
0.6154	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6805	Discontinued
0.614	Remote Similarity	NPD7444	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD5184	Approved
0.6138	Remote Similarity	NPD5182	Approved
0.6138	Remote Similarity	NPD5185	Approved
0.6126	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD3509	Approved
0.6122	Remote Similarity	NPD3510	Approved
0.6119	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD6395	Phase 2
0.6119	Remote Similarity	NPD1663	Discontinued
0.61	Remote Similarity	NPD5639	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD5263	Approved
0.6095	Remote Similarity	NPD5600	Discontinued
0.6093	Remote Similarity	NPD7683	Discontinued
0.6091	Remote Similarity	NPD2426	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD5042	Phase 1
0.6076	Remote Similarity	NPD6165	Phase 2
0.6076	Remote Similarity	NPD6164	Phase 2
0.6073	Remote Similarity	NPD6073	Approved
0.6073	Remote Similarity	NPD7944	Discontinued
0.6061	Remote Similarity	NPD7543	Phase 2
0.6059	Remote Similarity	NPD33	Approved
0.6059	Remote Similarity	NPD4393	Approved
0.6058	Remote Similarity	NPD3824	Phase 1
0.6055	Remote Similarity	NPD6200	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD6238	Discontinued
0.6054	Remote Similarity	NPD7727	Phase 2
0.6054	Remote Similarity	NPD6792	Phase 3
0.6053	Remote Similarity	NPD4153	Approved
0.6051	Remote Similarity	NPD5265	Approved
0.6051	Remote Similarity	NPD2820	Phase 3
0.6051	Remote Similarity	NPD5264	Approved
0.6048	Remote Similarity	NPD4091	Approved
0.6044	Remote Similarity	NPD6644	Discontinued
0.6043	Remote Similarity	NPD3040	Approved
0.6043	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4126	Approved
0.6038	Remote Similarity	NPD3227	Phase 2
0.6038	Remote Similarity	NPD4330	Approved
0.6038	Remote Similarity	NPD4329	Approved
0.6036	Remote Similarity	NPD7308	Discontinued
0.6035	Remote Similarity	NPD7666	Phase 3
0.6035	Remote Similarity	NPD7665	Phase 2
0.6029	Remote Similarity	NPD7854	Phase 2
0.6026	Remote Similarity	NPD7470	Discontinued
0.6019	Remote Similarity	NPD6483	Approved
0.6019	Remote Similarity	NPD3993	Approved
0.6019	Remote Similarity	NPD4092	Approved
0.6019	Remote Similarity	NPD6484	Approved
0.6019	Remote Similarity	NPD3995	Approved
0.6019	Remote Similarity	NPD3449	Discontinued
0.6019	Remote Similarity	NPD4317	Approved
0.6019	Remote Similarity	NPD3992	Approved
0.6019	Remote Similarity	NPD3991	Approved
0.6019	Remote Similarity	NPD3996	Approved
0.6019	Remote Similarity	NPD3994	Approved
0.6019	Remote Similarity	NPD3792	Approved
0.6018	Remote Similarity	NPD7001	Phase 3
0.6017	Remote Similarity	NPD7717	Approved
0.6017	Remote Similarity	NPD7716	Approved
0.6009	Remote Similarity	NPD2327	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD4520	Approved
0.6	Remote Similarity	NPD5466	Approved
0.6	Remote Similarity	NPD2365	Approved
0.6	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7205	Discontinued
0.5991	Remote Similarity	NPD3998	Approved
0.5991	Remote Similarity	NPD8025	Phase 2
0.5991	Remote Similarity	NPD3999	Approved
0.5991	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD6596	Phase 2
0.5991	Remote Similarity	NPD3997	Approved
0.599	Remote Similarity	NPD5606	Discontinued
0.5983	Remote Similarity	NPD7168	Phase 3
0.5982	Remote Similarity	NPD3479	Discontinued
0.5981	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD8272	Phase 2
0.5973	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD5426	Phase 3
0.597	Remote Similarity	NPD8315	Phase 1
0.5969	Remote Similarity	NPD3508	Approved
0.5966	Remote Similarity	NPD8271	Discontinued
0.5964	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD7617	Discontinued
0.5961	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.5959	Remote Similarity	NPD5318	Discontinued
0.5957	Remote Similarity	NPD4177	Approved
0.5957	Remote Similarity	NPD4175	Approved
0.5952	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD6173	Approved
0.5947	Remote Similarity	NPD6260	Discontinued
0.5946	Remote Similarity	NPD3071	Approved
0.5946	Remote Similarity	NPD3828	Approved
0.5946	Remote Similarity	NPD3073	Approved
0.5946	Remote Similarity	NPD3072	Approved
0.5945	Remote Similarity	NPD6891	Phase 2
0.5945	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.5944	Remote Similarity	NPD8250	Phase 2
0.5943	Remote Similarity	NPD6982	Phase 2
0.5938	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD6659	Phase 2
0.5935	Remote Similarity	NPD7432	Phase 2
0.5928	Remote Similarity	NPD7618	Phase 3
0.5928	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD7619	Phase 3
0.5926	Remote Similarity	NPD4676	Approved
0.5924	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD3522	Approved
0.5921	Remote Similarity	NPD6518	Discontinued
0.5919	Remote Similarity	NPD5196	Approved
0.5919	Remote Similarity	NPD7995	Phase 2
0.5919	Remote Similarity	NPD5194	Approved
0.5919	Remote Similarity	NPD5197	Approved
0.5918	Remote Similarity	NPD6566	Discontinued
0.5917	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD6368	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