NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	696.1
Volume:	608.265
LogP:	3.437
LogD:	2.241
LogS:	-4.538
# Rotatable Bonds:	1
TPSA:	145.76
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	12
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.32
Synthetic Accessibility Score:	7.907
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:	-5.785
MDCK Permeability:	1.219550449604867e-05
Pgp-inhibitor:	0.976
Pgp-substrate:	0.814
Human Intestinal Absorption (HIA):	0.757
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.151
Plasma Protein Binding (PPB):	80.17511749267578%
Volume Distribution (VD):	1.241
Pgp-substrate:	13.418949127197266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.957
CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.98
CYP2C9-substrate:	0.105
CYP2D6-inhibitor:	0.367
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.948
CYP3A4-substrate:	0.988

ADMET: Excretion

Clearance (CL):	7.134
Half-life (T1/2):	0.036

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.783
Maximum Recommended Daily Dose:	0.339
Skin Sensitization:	0.919
Carcinogencity:	0.367
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.179

Download Data

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

Natural Product: NPC477178

Natural Product ID:	NPC477178
*Common Name:**	(1S,2S,3S,11R,14S)-2-hydroxy-3-[(1S,2S,3S,11R,14R)-2-hydroxy-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]-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
IUPAC Name:	(1S,2S,3S,11R,14S)-2-hydroxy-3-[(1S,2S,3S,11R,14R)-2-hydroxy-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]-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:
Standard InCHIKey:	IMGTYEJTVRXGLW-DGCYEQIUSA-N
Standard InCHI:	InChI=1S/C30H28N6O6S4/c1-25-21(39)35-19-27(13-9-5-7-11-15(13)31-19,17(37)29(35,45-43-25)23(41)33(25)3)28-14-10-6-8-12-16(14)32-20(28)36-22(40)26(2)34(4)24(42)30(36,18(28)38)46-44-26/h5-12,17-20,31-32,37-38H,1-4H3/t17-,18-,19+,20+,25-,26+,27+,28+,29-,30-/m0/s1
SMILES:	C[C@@]12C(=O)N3[C@@H]4[C@]([C@@H]([C@@]3(C(=O)N1C)SS2)O)(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:	44584289
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	=	30	ug/ml	PMID[16252916]
NPT1272	Organism	Panagrellus redivivus	Panagrellus redivivus	ED50	=	80	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 NPC477178 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	297
0.1-0.2	1547
0.2-0.3	6856
0.3-0.4	24446
0.4-0.5	6541
0.5-0.6	2434
0.6-0.7	488
0.7-0.8	65
0.8-0.85	2
0.85-0.9	0
0.9-0.95	9
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC254850
1.0	High Similarity	NPC477181
1.0	High Similarity	NPC477180
0.9945	High Similarity	NPC470490
0.9945	High Similarity	NPC477179
0.9837	High Similarity	NPC475259
0.9837	High Similarity	NPC471945
0.9837	High Similarity	NPC471950
0.9731	High Similarity	NPC191817
0.9731	High Similarity	NPC475359
0.9728	High Similarity	NPC477173
0.9728	High Similarity	NPC477174
0.9676	High Similarity	NPC470488
0.9572	High Similarity	NPC471946
0.9572	High Similarity	NPC471951
0.9312	High Similarity	NPC470491
0.9282	High Similarity	NPC128582
0.9053	High Similarity	NPC470489
0.7991	Intermediate Similarity	NPC475859
0.7991	Intermediate Similarity	NPC475969
0.7944	Intermediate Similarity	NPC470730
0.7944	Intermediate Similarity	NPC477175
0.7872	Intermediate Similarity	NPC242269
0.787	Intermediate Similarity	NPC165743
0.7772	Intermediate Similarity	NPC276085
0.7742	Intermediate Similarity	NPC474877
0.7742	Intermediate Similarity	NPC477177
0.7734	Intermediate Similarity	NPC471436
0.7696	Intermediate Similarity	NPC470729
0.7696	Intermediate Similarity	NPC477176
0.7692	Intermediate Similarity	NPC307396
0.7677	Intermediate Similarity	NPC276430
0.7671	Intermediate Similarity	NPC63279
0.7636	Intermediate Similarity	NPC297642
0.7581	Intermediate Similarity	NPC327095
0.7581	Intermediate Similarity	NPC312942
0.7513	Intermediate Similarity	NPC259626
0.7513	Intermediate Similarity	NPC471124
0.7462	Intermediate Similarity	NPC2933
0.7433	Intermediate Similarity	NPC222029
0.7411	Intermediate Similarity	NPC256288
0.7409	Intermediate Similarity	NPC285622
0.7394	Intermediate Similarity	NPC471122
0.7385	Intermediate Similarity	NPC40455
0.7383	Intermediate Similarity	NPC470731
0.73	Intermediate Similarity	NPC473615
0.7264	Intermediate Similarity	NPC229484
0.7263	Intermediate Similarity	NPC309531
0.7263	Intermediate Similarity	NPC472102
0.7252	Intermediate Similarity	NPC297862
0.7236	Intermediate Similarity	NPC477159
0.7228	Intermediate Similarity	NPC292675
0.7173	Intermediate Similarity	NPC68650
0.7157	Intermediate Similarity	NPC476441
0.7156	Intermediate Similarity	NPC329833
0.715	Intermediate Similarity	NPC472106
0.715	Intermediate Similarity	NPC162440
0.7143	Intermediate Similarity	NPC470301
0.7143	Intermediate Similarity	NPC470732
0.7117	Intermediate Similarity	NPC19170
0.7067	Intermediate Similarity	NPC90967
0.7059	Intermediate Similarity	NPC284706
0.7051	Intermediate Similarity	NPC471663
0.7047	Intermediate Similarity	NPC472120
0.7047	Intermediate Similarity	NPC472101
0.7047	Intermediate Similarity	NPC176983
0.7047	Intermediate Similarity	NPC286871
0.7042	Intermediate Similarity	NPC225400
0.7019	Intermediate Similarity	NPC470787
0.7019	Intermediate Similarity	NPC472540
0.7019	Intermediate Similarity	NPC472539
0.7009	Intermediate Similarity	NPC471155
0.7009	Intermediate Similarity	NPC472538
0.7009	Intermediate Similarity	NPC470786
0.7	Intermediate Similarity	NPC106118
0.6996	Remote Similarity	NPC476817
0.6986	Remote Similarity	NPC472541
0.6986	Remote Similarity	NPC472542
0.6986	Remote Similarity	NPC471199
0.6984	Remote Similarity	NPC66936
0.6977	Remote Similarity	NPC270241
0.697	Remote Similarity	NPC476425
0.6954	Remote Similarity	NPC472118
0.6939	Remote Similarity	NPC472115
0.6939	Remote Similarity	NPC472114
0.6937	Remote Similarity	NPC272174
0.6935	Remote Similarity	NPC470548
0.6931	Remote Similarity	NPC476428
0.6915	Remote Similarity	NPC475094
0.6884	Remote Similarity	NPC473880
0.6881	Remote Similarity	NPC166169
0.6872	Remote Similarity	NPC472117
0.686	Remote Similarity	NPC105055
0.686	Remote Similarity	NPC22689
0.6853	Remote Similarity	NPC214960
0.6853	Remote Similarity	NPC279527
0.685	Remote Similarity	NPC475097
0.6839	Remote Similarity	NPC29285
0.6831	Remote Similarity	NPC471123
0.683	Remote Similarity	NPC474896
0.682	Remote Similarity	NPC285192
0.681	Remote Similarity	NPC34717
0.6808	Remote Similarity	NPC475489
0.6804	Remote Similarity	NPC113946
0.6802	Remote Similarity	NPC471197
0.68	Remote Similarity	NPC31097
0.68	Remote Similarity	NPC251212
0.68	Remote Similarity	NPC214626
0.68	Remote Similarity	NPC253987
0.68	Remote Similarity	NPC139085
0.68	Remote Similarity	NPC473743
0.68	Remote Similarity	NPC177261
0.6789	Remote Similarity	NPC109787
0.6779	Remote Similarity	NPC473298
0.6778	Remote Similarity	NPC14812
0.6771	Remote Similarity	NPC471198
0.6763	Remote Similarity	NPC181928
0.6748	Remote Similarity	NPC476095
0.6742	Remote Similarity	NPC473006
0.6717	Remote Similarity	NPC475420
0.6713	Remote Similarity	NPC295548
0.67	Remote Similarity	NPC476326
0.6696	Remote Similarity	NPC248601
0.6667	Remote Similarity	NPC52262
0.6667	Remote Similarity	NPC469560
0.6667	Remote Similarity	NPC473329
0.6667	Remote Similarity	NPC355
0.6667	Remote Similarity	NPC219397
0.6651	Remote Similarity	NPC221687
0.6649	Remote Similarity	NPC478076
0.6638	Remote Similarity	NPC301501
0.6636	Remote Similarity	NPC107077
0.6636	Remote Similarity	NPC223791
0.6634	Remote Similarity	NPC286994
0.6633	Remote Similarity	NPC469898
0.6618	Remote Similarity	NPC302235
0.6597	Remote Similarity	NPC264589
0.6585	Remote Similarity	NPC99043
0.6585	Remote Similarity	NPC218594
0.658	Remote Similarity	NPC318086
0.6575	Remote Similarity	NPC145754
0.6561	Remote Similarity	NPC162860
0.6555	Remote Similarity	NPC469452
0.6553	Remote Similarity	NPC478028
0.6552	Remote Similarity	NPC223242
0.6544	Remote Similarity	NPC471512
0.6542	Remote Similarity	NPC97100
0.6542	Remote Similarity	NPC473375
0.654	Remote Similarity	NPC469450
0.6537	Remote Similarity	NPC260075
0.6533	Remote Similarity	NPC85651
0.6533	Remote Similarity	NPC472121
0.6533	Remote Similarity	NPC99632
0.6533	Remote Similarity	NPC282339
0.6522	Remote Similarity	NPC122886
0.6519	Remote Similarity	NPC252794
0.6515	Remote Similarity	NPC36495
0.6515	Remote Similarity	NPC473003
0.6504	Remote Similarity	NPC15384
0.6504	Remote Similarity	NPC244425
0.65	Remote Similarity	NPC329932
0.6498	Remote Similarity	NPC478029
0.6496	Remote Similarity	NPC139373
0.6488	Remote Similarity	NPC469900
0.6488	Remote Similarity	NPC129624
0.6486	Remote Similarity	NPC477160
0.6485	Remote Similarity	NPC63047
0.6485	Remote Similarity	NPC475248
0.6485	Remote Similarity	NPC473000
0.6485	Remote Similarity	NPC469451
0.6482	Remote Similarity	NPC225319
0.6482	Remote Similarity	NPC315368
0.6481	Remote Similarity	NPC52557
0.6471	Remote Similarity	NPC54420
0.6459	Remote Similarity	NPC97584
0.6456	Remote Similarity	NPC131977
0.6438	Remote Similarity	NPC473005
0.6432	Remote Similarity	NPC469902
0.6429	Remote Similarity	NPC473002
0.6422	Remote Similarity	NPC138830
0.6418	Remote Similarity	NPC328270
0.6418	Remote Similarity	NPC313757
0.6414	Remote Similarity	NPC324850
0.6411	Remote Similarity	NPC159963
0.6406	Remote Similarity	NPC472103
0.6404	Remote Similarity	NPC477714
0.6398	Remote Similarity	NPC478077
0.6385	Remote Similarity	NPC473569
0.6382	Remote Similarity	NPC61013
0.6382	Remote Similarity	NPC469428
0.6382	Remote Similarity	NPC104345
0.6381	Remote Similarity	NPC245741
0.6378	Remote Similarity	NPC475763
0.6377	Remote Similarity	NPC473001
0.6368	Remote Similarity	NPC285841
0.6368	Remote Similarity	NPC469741
0.6368	Remote Similarity	NPC14994
0.6364	Remote Similarity	NPC155143
0.636	Remote Similarity	NPC470784
0.636	Remote Similarity	NPC477715

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 NPC477178 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	508
0.2-0.3	673
0.3-0.4	2123
0.4-0.5	3951
0.5-0.6	1641
0.6-0.7	84
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
0.7677	Intermediate Similarity	NPD8240	Discontinued
0.6829	Remote Similarity	NPD6557	Phase 2
0.6823	Remote Similarity	NPD4121	Phase 3
0.6823	Remote Similarity	NPD4120	Approved
0.6798	Remote Similarity	NPD6878	Phase 2
0.6798	Remote Similarity	NPD6879	Phase 2
0.6788	Remote Similarity	NPD5742	Approved
0.6788	Remote Similarity	NPD5743	Approved
0.6788	Remote Similarity	NPD5741	Approved
0.6718	Remote Similarity	NPD8630	Approved
0.6684	Remote Similarity	NPD3625	Discontinued
0.665	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5942	Approved
0.6615	Remote Similarity	NPD5941	Approved
0.6614	Remote Similarity	NPD5024	Approved
0.6603	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD7599	Phase 2
0.6505	Remote Similarity	NPD5774	Approved
0.6505	Remote Similarity	NPD5775	Approved
0.6502	Remote Similarity	NPD7595	Discontinued
0.6471	Remote Similarity	NPD8322	Phase 2
0.6465	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD8115	Approved
0.6455	Remote Similarity	NPD8114	Approved
0.6386	Remote Similarity	NPD4976	Discontinued
0.6359	Remote Similarity	NPD4682	Phase 2
0.6343	Remote Similarity	NPD4602	Approved
0.634	Remote Similarity	NPD7824	Approved
0.6337	Remote Similarity	NPD3790	Phase 2
0.6332	Remote Similarity	NPD7105	Phase 1
0.6329	Remote Similarity	NPD7950	Approved
0.6329	Remote Similarity	NPD7789	Approved
0.6329	Remote Similarity	NPD7952	Approved
0.6329	Remote Similarity	NPD7951	Approved
0.6329	Remote Similarity	NPD7790	Approved
0.6329	Remote Similarity	NPD7953	Approved
0.6329	Remote Similarity	NPD7791	Approved
0.6327	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD7600	Phase 2
0.6311	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5997	Discontinued
0.6276	Remote Similarity	NPD4432	Discontinued
0.6273	Remote Similarity	NPD4600	Approved
0.6273	Remote Similarity	NPD4601	Approved
0.6263	Remote Similarity	NPD6358	Phase 2
0.6263	Remote Similarity	NPD8400	Approved
0.6263	Remote Similarity	NPD8402	Approved
0.6263	Remote Similarity	NPD8401	Approved
0.6262	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6255	Remote Similarity	NPD7730	Approved
0.6255	Remote Similarity	NPD7731	Approved
0.6244	Remote Similarity	NPD7890	Discontinued
0.6244	Remote Similarity	NPD7817	Phase 1
0.6239	Remote Similarity	NPD7271	Approved
0.6237	Remote Similarity	NPD5918	Discontinued
0.622	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD8289	Discontinued
0.6211	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD7970	Approved
0.6201	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD6805	Discontinued
0.6188	Remote Similarity	NPD4514	Approved
0.6186	Remote Similarity	NPD6301	Phase 2
0.6182	Remote Similarity	NPD5856	Discontinued
0.6178	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD6295	Approved
0.6178	Remote Similarity	NPD6294	Approved
0.6175	Remote Similarity	NPD7570	Approved
0.6175	Remote Similarity	NPD7569	Approved
0.617	Remote Similarity	NPD5581	Approved
0.6162	Remote Similarity	NPD5748	Phase 2
0.6161	Remote Similarity	NPD3989	Phase 3
0.616	Remote Similarity	NPD7780	Approved
0.616	Remote Similarity	NPD7781	Approved
0.6139	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD7968	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD3990	Phase 3
0.6129	Remote Similarity	NPD5076	Approved
0.6129	Remote Similarity	NPD5077	Approved
0.6122	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7444	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5184	Approved
0.6105	Remote Similarity	NPD5182	Approved
0.6105	Remote Similarity	NPD5185	Approved
0.6099	Remote Similarity	NPD7727	Phase 2
0.6099	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD3510	Approved
0.6091	Remote Similarity	NPD3509	Approved
0.6089	Remote Similarity	NPD6644	Discontinued
0.6089	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD6395	Phase 2
0.6089	Remote Similarity	NPD1663	Discontinued
0.607	Remote Similarity	NPD5639	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD5600	Discontinued
0.6065	Remote Similarity	NPD7683	Discontinued
0.6064	Remote Similarity	NPD5263	Approved
0.6061	Remote Similarity	NPD2426	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5042	Phase 1
0.605	Remote Similarity	NPD6165	Phase 2
0.605	Remote Similarity	NPD6164	Phase 2
0.6045	Remote Similarity	NPD7944	Discontinued
0.6042	Remote Similarity	NPD6073	Approved
0.6034	Remote Similarity	NPD7543	Phase 2
0.6029	Remote Similarity	NPD33	Approved
0.6029	Remote Similarity	NPD3824	Phase 1
0.6029	Remote Similarity	NPD4393	Approved
0.6027	Remote Similarity	NPD6238	Discontinued
0.6027	Remote Similarity	NPD6200	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD6792	Phase 3
0.6021	Remote Similarity	NPD4153	Approved
0.602	Remote Similarity	NPD2820	Phase 3
0.602	Remote Similarity	NPD5264	Approved
0.602	Remote Similarity	NPD5265	Approved
0.6019	Remote Similarity	NPD4091	Approved
0.6018	Remote Similarity	NPD8272	Phase 2
0.6017	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD3040	Approved
0.601	Remote Similarity	NPD4126	Approved
0.6009	Remote Similarity	NPD7308	Discontinued
0.6009	Remote Similarity	NPD7665	Phase 2
0.6009	Remote Similarity	NPD3227	Phase 2
0.6009	Remote Similarity	NPD4329	Approved
0.6009	Remote Similarity	NPD7666	Phase 3
0.6009	Remote Similarity	NPD4330	Approved
0.6	Remote Similarity	NPD7470	Discontinued
0.6	Remote Similarity	NPD7854	Phase 2
0.5992	Remote Similarity	NPD7717	Approved
0.5992	Remote Similarity	NPD7716	Approved
0.5991	Remote Similarity	NPD3996	Approved
0.5991	Remote Similarity	NPD3995	Approved
0.5991	Remote Similarity	NPD6484	Approved
0.5991	Remote Similarity	NPD3993	Approved
0.5991	Remote Similarity	NPD7001	Phase 3
0.5991	Remote Similarity	NPD4092	Approved
0.5991	Remote Similarity	NPD4317	Approved
0.5991	Remote Similarity	NPD3449	Discontinued
0.5991	Remote Similarity	NPD3792	Approved
0.5991	Remote Similarity	NPD3994	Approved
0.5991	Remote Similarity	NPD3991	Approved
0.5991	Remote Similarity	NPD6483	Approved
0.5991	Remote Similarity	NPD3992	Approved
0.5984	Remote Similarity	NPD8250	Phase 2
0.5983	Remote Similarity	NPD4520	Approved
0.5982	Remote Similarity	NPD2327	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD7205	Discontinued
0.5972	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD5466	Approved
0.5972	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD2365	Approved
0.5966	Remote Similarity	NPD6596	Phase 2
0.5965	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.5964	Remote Similarity	NPD5194	Approved
0.5964	Remote Similarity	NPD5197	Approved
0.5964	Remote Similarity	NPD5196	Approved
0.5963	Remote Similarity	NPD8025	Phase 2
0.5962	Remote Similarity	NPD3999	Approved
0.5962	Remote Similarity	NPD3998	Approved
0.5962	Remote Similarity	NPD3997	Approved
0.5961	Remote Similarity	NPD5606	Discontinued
0.5957	Remote Similarity	NPD7168	Phase 3
0.5955	Remote Similarity	NPD3479	Discontinued
0.5953	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD5426	Phase 3
0.5947	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD8315	Phase 1
0.594	Remote Similarity	NPD8271	Discontinued
0.5939	Remote Similarity	NPD3508	Approved
0.5938	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD7617	Discontinued
0.5931	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD5318	Discontinued
0.5926	Remote Similarity	NPD4177	Approved
0.5926	Remote Similarity	NPD4175	Approved
0.5924	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD6173	Approved
0.5921	Remote Similarity	NPD6260	Discontinued
0.5919	Remote Similarity	NPD3828	Approved
0.5918	Remote Similarity	NPD6982	Phase 2
0.5917	Remote Similarity	NPD6891	Phase 2
0.5917	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD3073	Approved
0.5914	Remote Similarity	NPD3071	Approved
0.5914	Remote Similarity	NPD3072	Approved
0.5911	Remote Similarity	NPD7432	Phase 2
0.5909	Remote Similarity	NPD6659	Phase 2
0.5907	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.5901	Remote Similarity	NPD7619	Phase 3
0.5901	Remote Similarity	NPD7618	Phase 3
0.5897	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD3522	Approved
0.5895	Remote Similarity	NPD4676	Approved
0.5895	Remote Similarity	NPD6518	Discontinued
0.5893	Remote Similarity	NPD7995	Phase 2
0.589	Remote Similarity	NPD6965	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