NPASS Compound

Structure

NPC43463 OpenBabel07101719512D 35 37 0 0 1 0 0 0 0 0999 V2000 1.5388 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5963 0.2579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4049 2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6923 1.8035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9049 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6453 -0.0511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4373 -1.0292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9049 3.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5013 1.2158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9021 0.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9049 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 24 1 0 0 0 0 7 25 1 0 0 0 0 8 26 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 25 1 0 0 0 0 11 17 1 0 0 0 0 11 26 1 0 0 0 0 12 24 1 0 0 0 0 14 27 2 0 0 0 0 14 32 1 0 0 0 0 15 28 2 0 0 0 0 15 34 1 0 0 0 0 16 29 2 0 0 0 0 16 35 1 0 0 0 0 17 20 1 0 0 0 0 17 30 1 1 0 0 0 18 12 1 6 0 0 0 18 22 1 0 0 0 0 18 33 1 0 0 0 0 19 24 1 6 0 0 0 19 32 1 0 0 0 0 20 13 1 6 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 26 1 0 0 0 0 23 25 1 0 0 0 0 23 33 1 0 0 0 0 24 31 1 0 0 0 0 25 34 1 0 0 0 0 26 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.28
Volume:	503.785
LogP:	2.669
LogD:	1.385
LogS:	-2.847
# Rotatable Bonds:	7
TPSA:	128.59
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.444
Synthetic Accessibility Score:	6.263
Fsp3:	0.885
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:	-5.081
MDCK Permeability:	8.494395297020674e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.068
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.289

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	52.47288513183594%
Volume Distribution (VD):	1.409
Pgp-substrate:	23.44317626953125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.048
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.705
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.327
CYP3A4-substrate:	0.479

ADMET: Excretion

Clearance (CL):	2.912
Half-life (T1/2):	0.822

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.793
Drug-inuced Liver Injury (DILI):	0.867
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.234
Carcinogencity:	0.104
Eye Corrosion:	0.014
Eye Irritation:	0.046
Respiratory Toxicity:	0.011

Download Data

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

Natural Product: NPC43463

Natural Product ID:	NPC43463
*Common Name:**	Simplexin I
IUPAC Name:	n.a.
Synonyms:	Simplexin I
Standard InCHIKey:	CMFFEVGUTXFGMQ-LXISNSFKSA-N
Standard InCHI:	InChI=1S/C26H42O9/c1-13(2)20-17(30)11-26(8,35-16(5)29)22-18-12-24(6,31)19(32-14(3)27)9-10-25(7,34-15(4)28)23(33-18)21(20)22/h13,17-23,30-31H,9-12H2,1-8H3/t17-,18-,19+,20+,21-,22-,23-,24+,25-,26-/m1/s1
SMILES:	CC(C)[C@H]1[C@@H](C[C@](C)([C@@H]2[C@H]3C[C@@](C)([C@H](CC[C@](C)([C@@H]([C@H]12)O3)OC(=O)C)OC(=O)C)O)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL563729
PubChem CID:	44179337
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002916] Eunicellane and asbestinane diterpenoids

*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
NPO6535	Klyxum simplex	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19391605]
NPO6535	Klyxum simplex	Species	Alcyoniidae	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
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1184	Cell Line	Daoy	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[495415]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[495415]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[495415]
NPT1171	Cell Line	HEp-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[495415]

☑ 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 NPC43463 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	377
0.1-0.2	3454
0.2-0.3	10262
0.3-0.4	13691
0.4-0.5	6617
0.5-0.6	6779
0.6-0.7	1346
0.7-0.8	126
0.8-0.85	24
0.85-0.9	11
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9722	High Similarity	NPC136424
0.96	High Similarity	NPC211049
0.9467	High Similarity	NPC186594
0.9459	High Similarity	NPC252483
0.9459	High Similarity	NPC191345
0.9342	High Similarity	NPC116320
0.9342	High Similarity	NPC119922
0.9324	High Similarity	NPC476719
0.9221	High Similarity	NPC216800
0.8974	High Similarity	NPC477447
0.8974	High Similarity	NPC470155
0.8974	High Similarity	NPC477446
0.8889	High Similarity	NPC471377
0.8846	High Similarity	NPC470156
0.8846	High Similarity	NPC470154
0.8784	High Similarity	NPC476718
0.8765	High Similarity	NPC246347
0.8765	High Similarity	NPC228593
0.8765	High Similarity	NPC279260
0.8765	High Similarity	NPC235196
0.8718	High Similarity	NPC472943
0.8718	High Similarity	NPC472951
0.8642	High Similarity	NPC93616
0.8642	High Similarity	NPC476715
0.8434	Intermediate Similarity	NPC44538
0.8353	Intermediate Similarity	NPC470262
0.8333	Intermediate Similarity	NPC75443
0.8333	Intermediate Similarity	NPC470260
0.8313	Intermediate Similarity	NPC477283
0.8313	Intermediate Similarity	NPC155531
0.8313	Intermediate Similarity	NPC215968
0.8313	Intermediate Similarity	NPC475684
0.8293	Intermediate Similarity	NPC18953
0.8289	Intermediate Similarity	NPC123122
0.8256	Intermediate Similarity	NPC91251
0.8256	Intermediate Similarity	NPC41838
0.8235	Intermediate Similarity	NPC291875
0.8214	Intermediate Similarity	NPC213658
0.8214	Intermediate Similarity	NPC62202
0.8214	Intermediate Similarity	NPC110365
0.8214	Intermediate Similarity	NPC45833
0.8193	Intermediate Similarity	NPC471379
0.8193	Intermediate Similarity	NPC196911
0.8148	Intermediate Similarity	NPC118116
0.814	Intermediate Similarity	NPC312471
0.814	Intermediate Similarity	NPC471378
0.8118	Intermediate Similarity	NPC476723
0.8118	Intermediate Similarity	NPC476724
0.8118	Intermediate Similarity	NPC92370
0.8095	Intermediate Similarity	NPC471410
0.8095	Intermediate Similarity	NPC471411
0.8077	Intermediate Similarity	NPC472950
0.8077	Intermediate Similarity	NPC472952
0.8049	Intermediate Similarity	NPC60018
0.8049	Intermediate Similarity	NPC154043
0.8049	Intermediate Similarity	NPC202688
0.8046	Intermediate Similarity	NPC122057
0.8023	Intermediate Similarity	NPC161560
0.7976	Intermediate Similarity	NPC266651
0.7955	Intermediate Similarity	NPC475307
0.7952	Intermediate Similarity	NPC69953
0.7952	Intermediate Similarity	NPC239308
0.7952	Intermediate Similarity	NPC111582
0.7952	Intermediate Similarity	NPC477285
0.7952	Intermediate Similarity	NPC5958
0.7949	Intermediate Similarity	NPC470151
0.7907	Intermediate Similarity	NPC470872
0.7907	Intermediate Similarity	NPC476435
0.7882	Intermediate Similarity	NPC476717
0.7841	Intermediate Similarity	NPC312805
0.7841	Intermediate Similarity	NPC473066
0.7831	Intermediate Similarity	NPC477284
0.7831	Intermediate Similarity	NPC477286
0.7831	Intermediate Similarity	NPC286719
0.7805	Intermediate Similarity	NPC474714
0.7791	Intermediate Similarity	NPC5943
0.7765	Intermediate Similarity	NPC235402
0.7765	Intermediate Similarity	NPC477445
0.7765	Intermediate Similarity	NPC476725
0.7738	Intermediate Similarity	NPC476721
0.7738	Intermediate Similarity	NPC127917
0.7738	Intermediate Similarity	NPC470261
0.7738	Intermediate Similarity	NPC29342
0.7738	Intermediate Similarity	NPC2572
0.7727	Intermediate Similarity	NPC470114
0.7722	Intermediate Similarity	NPC472944
0.7722	Intermediate Similarity	NPC472945
0.7711	Intermediate Similarity	NPC77003
0.7711	Intermediate Similarity	NPC190940
0.7701	Intermediate Similarity	NPC471221
0.7701	Intermediate Similarity	NPC476379
0.7701	Intermediate Similarity	NPC201607
0.7701	Intermediate Similarity	NPC56777
0.7683	Intermediate Similarity	NPC477282
0.7683	Intermediate Similarity	NPC81074
0.7674	Intermediate Similarity	NPC64862
0.7674	Intermediate Similarity	NPC131365
0.7634	Intermediate Similarity	NPC272223
0.7632	Intermediate Similarity	NPC476928
0.7619	Intermediate Similarity	NPC103171
0.7619	Intermediate Similarity	NPC208912
0.7619	Intermediate Similarity	NPC2096
0.7609	Intermediate Similarity	NPC111348
0.759	Intermediate Similarity	NPC471217
0.759	Intermediate Similarity	NPC186588
0.759	Intermediate Similarity	NPC471216
0.7561	Intermediate Similarity	NPC272841
0.7556	Intermediate Similarity	NPC182740
0.7556	Intermediate Similarity	NPC256104
0.7556	Intermediate Similarity	NPC122083
0.7556	Intermediate Similarity	NPC211845
0.7531	Intermediate Similarity	NPC293223
0.7529	Intermediate Similarity	NPC474346
0.7529	Intermediate Similarity	NPC241959
0.7529	Intermediate Similarity	NPC474253
0.7529	Intermediate Similarity	NPC474284
0.7529	Intermediate Similarity	NPC475820
0.7529	Intermediate Similarity	NPC213737
0.75	Intermediate Similarity	NPC166250
0.75	Intermediate Similarity	NPC203434
0.75	Intermediate Similarity	NPC237071
0.75	Intermediate Similarity	NPC475743
0.75	Intermediate Similarity	NPC71541
0.75	Intermediate Similarity	NPC238796
0.75	Intermediate Similarity	NPC309656
0.75	Intermediate Similarity	NPC73515
0.75	Intermediate Similarity	NPC116683
0.7473	Intermediate Similarity	NPC151214
0.7473	Intermediate Similarity	NPC191915
0.7471	Intermediate Similarity	NPC103782
0.7471	Intermediate Similarity	NPC114378
0.7471	Intermediate Similarity	NPC268633
0.747	Intermediate Similarity	NPC477287
0.747	Intermediate Similarity	NPC476176
0.7447	Intermediate Similarity	NPC188968
0.7444	Intermediate Similarity	NPC219516
0.7442	Intermediate Similarity	NPC477434
0.7442	Intermediate Similarity	NPC473299
0.7439	Intermediate Similarity	NPC64081
0.7439	Intermediate Similarity	NPC11907
0.7439	Intermediate Similarity	NPC474574
0.7439	Intermediate Similarity	NPC133596
0.7423	Intermediate Similarity	NPC470263
0.7416	Intermediate Similarity	NPC477443
0.7416	Intermediate Similarity	NPC477440
0.7407	Intermediate Similarity	NPC36479
0.7407	Intermediate Similarity	NPC186851
0.7391	Intermediate Similarity	NPC94582
0.7391	Intermediate Similarity	NPC292178
0.7391	Intermediate Similarity	NPC57964
0.7391	Intermediate Similarity	NPC86893
0.7391	Intermediate Similarity	NPC476720
0.7386	Intermediate Similarity	NPC472396
0.7381	Intermediate Similarity	NPC16449
0.7368	Intermediate Similarity	NPC475574
0.7349	Intermediate Similarity	NPC471045
0.7349	Intermediate Similarity	NPC177343
0.734	Intermediate Similarity	NPC209798
0.734	Intermediate Similarity	NPC471375
0.734	Intermediate Similarity	NPC471374
0.7333	Intermediate Similarity	NPC18536
0.7333	Intermediate Similarity	NPC477442
0.7333	Intermediate Similarity	NPC477433
0.7333	Intermediate Similarity	NPC50443
0.7333	Intermediate Similarity	NPC477444
0.7326	Intermediate Similarity	NPC15091
0.7317	Intermediate Similarity	NPC107963
0.7312	Intermediate Similarity	NPC292718
0.7312	Intermediate Similarity	NPC156377
0.7312	Intermediate Similarity	NPC235109
0.7312	Intermediate Similarity	NPC252056
0.7312	Intermediate Similarity	NPC169270
0.7312	Intermediate Similarity	NPC129569
0.7312	Intermediate Similarity	NPC111834
0.7312	Intermediate Similarity	NPC296936
0.7312	Intermediate Similarity	NPC306797
0.7284	Intermediate Similarity	NPC308489
0.7273	Intermediate Similarity	NPC107603
0.7273	Intermediate Similarity	NPC214315
0.7273	Intermediate Similarity	NPC322922
0.7273	Intermediate Similarity	NPC321812
0.7273	Intermediate Similarity	NPC474008
0.7263	Intermediate Similarity	NPC51579
0.7263	Intermediate Similarity	NPC471428
0.7263	Intermediate Similarity	NPC471427
0.7263	Intermediate Similarity	NPC471426
0.7262	Intermediate Similarity	NPC220379
0.7253	Intermediate Similarity	NPC8729
0.7241	Intermediate Similarity	NPC65133
0.7241	Intermediate Similarity	NPC320824
0.7237	Intermediate Similarity	NPC94897
0.7237	Intermediate Similarity	NPC476702
0.7234	Intermediate Similarity	NPC254121
0.7234	Intermediate Similarity	NPC473244
0.7234	Intermediate Similarity	NPC274793
0.7229	Intermediate Similarity	NPC307865
0.7229	Intermediate Similarity	NPC171658
0.7229	Intermediate Similarity	NPC212453
0.7222	Intermediate Similarity	NPC82955
0.7215	Intermediate Similarity	NPC470833

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 NPC43463 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	453
0.1-0.2	3889
0.2-0.3	3217
0.3-0.4	940
0.4-0.5	414
0.5-0.6	224
0.6-0.7	12
0.7-0.8	1
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
0.7792	Intermediate Similarity	NPD7532	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD371	Approved
0.6932	Remote Similarity	NPD3669	Approved
0.6932	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6114	Approved
0.6744	Remote Similarity	NPD6697	Approved
0.6744	Remote Similarity	NPD6115	Approved
0.6744	Remote Similarity	NPD6118	Approved
0.6667	Remote Similarity	NPD1811	Approved
0.6667	Remote Similarity	NPD1810	Approved
0.6632	Remote Similarity	NPD8171	Discontinued
0.6628	Remote Similarity	NPD6116	Phase 1
0.6512	Remote Similarity	NPD6117	Approved
0.65	Remote Similarity	NPD1700	Approved
0.65	Remote Similarity	NPD5344	Discontinued
0.6442	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6928	Phase 2
0.6381	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.631	Remote Similarity	NPD2254	Approved
0.631	Remote Similarity	NPD2687	Approved
0.631	Remote Similarity	NPD2686	Approved
0.6279	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD7328	Approved
0.6216	Remote Similarity	NPD7327	Approved
0.6173	Remote Similarity	NPD7909	Approved
0.6168	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7516	Approved
0.6154	Remote Similarity	NPD1780	Approved
0.6154	Remote Similarity	NPD1779	Approved
0.6147	Remote Similarity	NPD8133	Approved
0.6078	Remote Similarity	NPD6648	Approved
0.6053	Remote Similarity	NPD8378	Approved
0.6053	Remote Similarity	NPD8380	Approved
0.6053	Remote Similarity	NPD8296	Approved
0.6053	Remote Similarity	NPD8335	Approved
0.6053	Remote Similarity	NPD8379	Approved
0.6023	Remote Similarity	NPD3703	Phase 2
0.598	Remote Similarity	NPD7638	Approved
0.598	Remote Similarity	NPD4225	Approved
0.5972	Remote Similarity	NPD384	Approved
0.5972	Remote Similarity	NPD385	Approved
0.5965	Remote Similarity	NPD8294	Approved
0.5965	Remote Similarity	NPD8377	Approved
0.5922	Remote Similarity	NPD7640	Approved
0.5922	Remote Similarity	NPD7639	Approved
0.5913	Remote Similarity	NPD6921	Approved
0.5913	Remote Similarity	NPD8033	Approved
0.5888	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD8034	Phase 2
0.5859	Remote Similarity	NPD8035	Phase 2
0.5844	Remote Similarity	NPD3728	Approved
0.5844	Remote Similarity	NPD3730	Approved
0.5843	Remote Similarity	NPD3702	Approved
0.5841	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6686	Approved
0.5833	Remote Similarity	NPD386	Approved
0.5833	Remote Similarity	NPD388	Approved
0.5826	Remote Similarity	NPD6319	Approved
0.5814	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.581	Remote Similarity	NPD7632	Discontinued
0.5776	Remote Similarity	NPD7503	Approved
0.5773	Remote Similarity	NPD7524	Approved
0.5766	Remote Similarity	NPD8297	Approved
0.5758	Remote Similarity	NPD3168	Discontinued
0.5758	Remote Similarity	NPD7838	Discovery
0.5758	Remote Similarity	NPD6698	Approved
0.5758	Remote Similarity	NPD46	Approved
0.5752	Remote Similarity	NPD6940	Discontinued
0.5747	Remote Similarity	NPD4787	Phase 1
0.5729	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4632	Approved
0.5714	Remote Similarity	NPD7507	Approved
0.5702	Remote Similarity	NPD7319	Approved
0.5699	Remote Similarity	NPD7525	Registered
0.5696	Remote Similarity	NPD2267	Suspended
0.5682	Remote Similarity	NPD5777	Approved
0.5679	Remote Similarity	NPD3198	Approved
0.5652	Remote Similarity	NPD4802	Phase 2
0.5652	Remote Similarity	NPD4238	Approved
0.5648	Remote Similarity	NPD7128	Approved
0.5648	Remote Similarity	NPD6675	Approved
0.5648	Remote Similarity	NPD5739	Approved
0.5648	Remote Similarity	NPD6402	Approved
0.5636	Remote Similarity	NPD6372	Approved
0.5636	Remote Similarity	NPD6373	Approved
0.563	Remote Similarity	NPD7492	Approved
0.5625	Remote Similarity	NPD7338	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