NPASS Compound

Structure

NPC471343 OpenBabel07101718222D 29 31 0 0 1 0 0 0 0 0999 V2000 4.4392 -0.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4495 -2.4495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6712 2.3052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6712 2.3052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2843 0.8376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4392 3.4392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0372 -0.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1712 -0.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4392 1.4392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9319 -0.5176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2071 1.5731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0372 0.9392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2071 1.5731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4392 2.4392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3052 -0.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4836 -2.1907 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3052 0.9392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2247 -1.2247 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7071 2.4392 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7765 -2.8978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1712 1.4392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 0.7071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5731 2.9392 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0353 -3.8637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1895 -2.6390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7071 3.4392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2588 -0.9659 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 1 16 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 16 1 0 0 0 0 9 15 1 0 0 0 0 9 18 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 16 18 2 0 0 0 0 17 2 1 1 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 17 1 1 0 0 0 19 28 1 0 0 0 0 20 24 1 6 0 0 0 20 27 1 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 23 5 1 1 0 0 0 23 29 1 0 0 0 0 24 6 1 6 0 0 0 24 27 1 0 0 0 0 28 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.29
Volume:	436.669
LogP:	5.838
LogD:	3.795
LogS:	-4.006
# Rotatable Bonds:	8
TPSA:	68.29
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.311
Synthetic Accessibility Score:	4.883
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.958
MDCK Permeability:	2.0051678802701645e-05
Pgp-inhibitor:	0.95
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.124
Plasma Protein Binding (PPB):	96.11968994140625%
Volume Distribution (VD):	1.616
Pgp-substrate:	3.6976919174194336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.401
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.948
CYP2C9-inhibitor:	0.123
CYP2C9-substrate:	0.809
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.797
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.128

ADMET: Excretion

Clearance (CL):	7.038
Half-life (T1/2):	0.109

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.278
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.301
Maximum Recommended Daily Dose:	0.075
Skin Sensitization:	0.861
Carcinogencity:	0.398
Eye Corrosion:	0.812
Eye Irritation:	0.44
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC471343

Natural Product ID:	NPC471343
*Common Name:**	Rel-(-)-9,10-Epoxymuqubilin A
IUPAC Name:	(2R)-2-[(3S,6R)-6-methyl-6-[2-[(2S,3S)-3-methyl-3-[2-(2,6,6-trimethylcyclohexen-1-yl)ethyl]oxiran-2-yl]ethyl]dioxan-3-yl]propanoic acid
Synonyms:
Standard InCHIKey:	QVVWUQNRKZFZHV-XMPUZHHRSA-N
Standard InCHI:	InChI=1S/C24H40O5/c1-16-8-7-12-22(3,4)18(16)9-15-24(6)20(27-24)11-14-23(5)13-10-19(28-29-23)17(2)21(25)26/h17,19-20H,7-15H2,1-6H3,(H,25,26)/t17-,19+,20+,23+,24+/m1/s1
SMILES:	CC1=C(C(CCC1)(C)C)CCC2(C(O2)CCC3(CCC(OO3)C(C)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419353
PubChem CID:	73349169
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO5207	Diacarnus erythraeanus	Species	Podospongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11325240]
NPO5207	Diacarnus erythraeanus	Species	Podospongiidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[11325240]
NPO5207	Diacarnus erythraeanus	Species	Podospongiidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[23977995]

☑ 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	6

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	1000.0	nM	PMID[449792]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	4000.0	nM	PMID[449792]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3000.0	nM	PMID[449792]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	15000.0	nM	PMID[449792]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4000.0	nM	PMID[449792]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3000.0	nM	PMID[449792]

☑ 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 NPC471343 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	205
0.1-0.2	1597
0.2-0.3	5762
0.3-0.4	14376
0.4-0.5	8514
0.5-0.6	7582
0.6-0.7	4405
0.7-0.8	237
0.8-0.85	12
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8974	High Similarity	NPC59602
0.8974	High Similarity	NPC476987
0.8974	High Similarity	NPC152754
0.8889	High Similarity	NPC172309
0.8889	High Similarity	NPC14044
0.8889	High Similarity	NPC117960
0.8721	High Similarity	NPC471342
0.8721	High Similarity	NPC469866
0.8675	High Similarity	NPC476983
0.8675	High Similarity	NPC476100
0.8642	High Similarity	NPC254996
0.8642	High Similarity	NPC268502
0.8434	Intermediate Similarity	NPC476988
0.8415	Intermediate Similarity	NPC308545
0.8415	Intermediate Similarity	NPC82488
0.8372	Intermediate Similarity	NPC476104
0.8372	Intermediate Similarity	NPC476982
0.8372	Intermediate Similarity	NPC475181
0.8372	Intermediate Similarity	NPC262085
0.8293	Intermediate Similarity	NPC470905
0.8293	Intermediate Similarity	NPC476986
0.8256	Intermediate Similarity	NPC471344
0.8171	Intermediate Similarity	NPC476325
0.8171	Intermediate Similarity	NPC476264
0.814	Intermediate Similarity	NPC475193
0.814	Intermediate Similarity	NPC120158
0.8118	Intermediate Similarity	NPC476984
0.8118	Intermediate Similarity	NPC475395
0.8049	Intermediate Similarity	NPC476985
0.8049	Intermediate Similarity	NPC475744
0.8049	Intermediate Similarity	NPC469514
0.8049	Intermediate Similarity	NPC474316
0.7952	Intermediate Similarity	NPC469867
0.7907	Intermediate Similarity	NPC476292
0.7907	Intermediate Similarity	NPC474605
0.7857	Intermediate Similarity	NPC121200
0.7816	Intermediate Similarity	NPC69469
0.7805	Intermediate Similarity	NPC330016
0.7791	Intermediate Similarity	NPC475481
0.7791	Intermediate Similarity	NPC327002
0.7791	Intermediate Similarity	NPC79277
0.7765	Intermediate Similarity	NPC246458
0.7753	Intermediate Similarity	NPC475753
0.7738	Intermediate Similarity	NPC281296
0.7738	Intermediate Similarity	NPC122847
0.7717	Intermediate Similarity	NPC36491
0.7692	Intermediate Similarity	NPC256902
0.7692	Intermediate Similarity	NPC118193
0.7684	Intermediate Similarity	NPC124246
0.7683	Intermediate Similarity	NPC167145
0.7674	Intermediate Similarity	NPC274522
0.7674	Intermediate Similarity	NPC476265
0.7647	Intermediate Similarity	NPC321514
0.764	Intermediate Similarity	NPC76333
0.7619	Intermediate Similarity	NPC474447
0.7558	Intermediate Similarity	NPC327674
0.7528	Intermediate Similarity	NPC469407
0.7526	Intermediate Similarity	NPC475156
0.7526	Intermediate Similarity	NPC473576
0.7525	Intermediate Similarity	NPC322903
0.75	Intermediate Similarity	NPC470587
0.75	Intermediate Similarity	NPC60718
0.75	Intermediate Similarity	NPC199445
0.75	Intermediate Similarity	NPC97577
0.7473	Intermediate Similarity	NPC197333
0.7449	Intermediate Similarity	NPC476246
0.7449	Intermediate Similarity	NPC477871
0.7449	Intermediate Similarity	NPC477870
0.7449	Intermediate Similarity	NPC476213
0.7447	Intermediate Similarity	NPC477435
0.7447	Intermediate Similarity	NPC477436
0.7436	Intermediate Similarity	NPC474552
0.7423	Intermediate Similarity	NPC222303
0.7412	Intermediate Similarity	NPC239127
0.7396	Intermediate Similarity	NPC469369
0.7396	Intermediate Similarity	NPC469528
0.7396	Intermediate Similarity	NPC471822
0.7391	Intermediate Similarity	NPC201046
0.7381	Intermediate Similarity	NPC474551
0.7374	Intermediate Similarity	NPC476235
0.7374	Intermediate Similarity	NPC476126
0.7374	Intermediate Similarity	NPC183571
0.7374	Intermediate Similarity	NPC283567
0.7368	Intermediate Similarity	NPC78580
0.7368	Intermediate Similarity	NPC23621
0.7368	Intermediate Similarity	NPC477439
0.7368	Intermediate Similarity	NPC184006
0.7363	Intermediate Similarity	NPC477993
0.7363	Intermediate Similarity	NPC477994
0.7363	Intermediate Similarity	NPC73038
0.7356	Intermediate Similarity	NPC113363
0.7347	Intermediate Similarity	NPC54705
0.7347	Intermediate Similarity	NPC167974
0.734	Intermediate Similarity	NPC150383
0.7327	Intermediate Similarity	NPC16313
0.7327	Intermediate Similarity	NPC9303
0.7327	Intermediate Similarity	NPC475802
0.7312	Intermediate Similarity	NPC474570
0.7312	Intermediate Similarity	NPC474700
0.7308	Intermediate Similarity	NPC317107
0.73	Intermediate Similarity	NPC69171
0.73	Intermediate Similarity	NPC474165
0.7294	Intermediate Similarity	NPC255060
0.7292	Intermediate Similarity	NPC108141
0.7292	Intermediate Similarity	NPC195715
0.7292	Intermediate Similarity	NPC473648
0.7292	Intermediate Similarity	NPC266899
0.7292	Intermediate Similarity	NPC37603
0.7292	Intermediate Similarity	NPC23241
0.7292	Intermediate Similarity	NPC471786
0.7292	Intermediate Similarity	NPC477437
0.7292	Intermediate Similarity	NPC477438
0.7283	Intermediate Similarity	NPC171722
0.7283	Intermediate Similarity	NPC86005
0.7283	Intermediate Similarity	NPC167877
0.7282	Intermediate Similarity	NPC475922
0.7273	Intermediate Similarity	NPC103634
0.7262	Intermediate Similarity	NPC474543
0.7262	Intermediate Similarity	NPC238425
0.7262	Intermediate Similarity	NPC472018
0.7255	Intermediate Similarity	NPC474421
0.7255	Intermediate Similarity	NPC326994
0.7255	Intermediate Similarity	NPC72813
0.7255	Intermediate Similarity	NPC324327
0.7255	Intermediate Similarity	NPC194620
0.7255	Intermediate Similarity	NPC112780
0.7253	Intermediate Similarity	NPC329738
0.725	Intermediate Similarity	NPC306805
0.725	Intermediate Similarity	NPC215987
0.725	Intermediate Similarity	NPC476330
0.7245	Intermediate Similarity	NPC164349
0.7245	Intermediate Similarity	NPC264378
0.7245	Intermediate Similarity	NPC475876
0.7238	Intermediate Similarity	NPC317687
0.7234	Intermediate Similarity	NPC48732
0.7234	Intermediate Similarity	NPC289213
0.7234	Intermediate Similarity	NPC232202
0.7228	Intermediate Similarity	NPC239162
0.7228	Intermediate Similarity	NPC470104
0.7228	Intermediate Similarity	NPC475036
0.7228	Intermediate Similarity	NPC146731
0.7222	Intermediate Similarity	NPC477373
0.7222	Intermediate Similarity	NPC475989
0.7216	Intermediate Similarity	NPC476797
0.7216	Intermediate Similarity	NPC120708
0.7216	Intermediate Similarity	NPC143446
0.7216	Intermediate Similarity	NPC471777
0.7216	Intermediate Similarity	NPC132824
0.7216	Intermediate Similarity	NPC327788
0.7212	Intermediate Similarity	NPC161816
0.7212	Intermediate Similarity	NPC115257
0.7204	Intermediate Similarity	NPC476706
0.7204	Intermediate Similarity	NPC183546
0.7204	Intermediate Similarity	NPC476707
0.7204	Intermediate Similarity	NPC294480
0.72	Intermediate Similarity	NPC22388
0.72	Intermediate Similarity	NPC475091
0.72	Intermediate Similarity	NPC475558
0.72	Intermediate Similarity	NPC473788
0.7191	Intermediate Similarity	NPC14203
0.7191	Intermediate Similarity	NPC229584
0.7188	Intermediate Similarity	NPC240617
0.7188	Intermediate Similarity	NPC174051
0.7188	Intermediate Similarity	NPC474963
0.7188	Intermediate Similarity	NPC67831
0.7188	Intermediate Similarity	NPC124207
0.7184	Intermediate Similarity	NPC94377
0.7184	Intermediate Similarity	NPC169888
0.7184	Intermediate Similarity	NPC474664
0.7184	Intermediate Similarity	NPC469916
0.7184	Intermediate Similarity	NPC472439
0.7184	Intermediate Similarity	NPC327286
0.7184	Intermediate Similarity	NPC233379
0.7184	Intermediate Similarity	NPC14862
0.7184	Intermediate Similarity	NPC55972
0.7184	Intermediate Similarity	NPC102843
0.7179	Intermediate Similarity	NPC472021
0.7174	Intermediate Similarity	NPC212843
0.7174	Intermediate Similarity	NPC229717
0.7174	Intermediate Similarity	NPC322159
0.7174	Intermediate Similarity	NPC470415
0.7174	Intermediate Similarity	NPC325594
0.7174	Intermediate Similarity	NPC324063
0.7172	Intermediate Similarity	NPC474718
0.717	Intermediate Similarity	NPC159333
0.7159	Intermediate Similarity	NPC622
0.7159	Intermediate Similarity	NPC276647
0.7158	Intermediate Similarity	NPC324341
0.7158	Intermediate Similarity	NPC228784
0.7158	Intermediate Similarity	NPC282616
0.7158	Intermediate Similarity	NPC966
0.7158	Intermediate Similarity	NPC73457
0.7158	Intermediate Similarity	NPC474631
0.7158	Intermediate Similarity	NPC6255
0.7158	Intermediate Similarity	NPC155120
0.7158	Intermediate Similarity	NPC235704
0.7158	Intermediate Similarity	NPC288833
0.7158	Intermediate Similarity	NPC470373
0.7158	Intermediate Similarity	NPC476417
0.7158	Intermediate Similarity	NPC475708

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 NPC471343 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	2165
0.2-0.3	3825
0.3-0.4	2001
0.4-0.5	523
0.5-0.6	369
0.6-0.7	82
0.7-0.8	5
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
0.7717	Intermediate Similarity	NPD6411	Approved
0.75	Intermediate Similarity	NPD6101	Approved
0.75	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5778	Approved
0.7447	Intermediate Similarity	NPD5779	Approved
0.7234	Intermediate Similarity	NPD46	Approved
0.7234	Intermediate Similarity	NPD6698	Approved
0.7083	Intermediate Similarity	NPD6399	Phase 3
0.701	Intermediate Similarity	NPD5282	Discontinued
0.6952	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7748	Approved
0.6804	Remote Similarity	NPD7983	Approved
0.6804	Remote Similarity	NPD7637	Suspended
0.68	Remote Similarity	NPD7902	Approved
0.68	Remote Similarity	NPD6083	Phase 2
0.68	Remote Similarity	NPD6084	Phase 2
0.6792	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5695	Phase 3
0.67	Remote Similarity	NPD7839	Suspended
0.6698	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6402	Approved
0.6633	Remote Similarity	NPD7515	Phase 2
0.6632	Remote Similarity	NPD5330	Approved
0.6632	Remote Similarity	NPD6684	Approved
0.6632	Remote Similarity	NPD7521	Approved
0.6632	Remote Similarity	NPD7334	Approved
0.6632	Remote Similarity	NPD7146	Approved
0.6632	Remote Similarity	NPD6409	Approved
0.663	Remote Similarity	NPD5369	Approved
0.6627	Remote Similarity	NPD7341	Phase 2
0.6604	Remote Similarity	NPD6412	Phase 2
0.6604	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6371	Approved
0.6569	Remote Similarity	NPD5696	Approved
0.6559	Remote Similarity	NPD6435	Approved
0.6542	Remote Similarity	NPD6899	Approved
0.6542	Remote Similarity	NPD7320	Approved
0.6542	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6881	Approved
0.6518	Remote Similarity	NPD7115	Discovery
0.6517	Remote Similarity	NPD8039	Approved
0.6509	Remote Similarity	NPD6008	Approved
0.65	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7900	Approved
0.6495	Remote Similarity	NPD6903	Approved
0.6495	Remote Similarity	NPD5737	Approved
0.6495	Remote Similarity	NPD6672	Approved
0.6495	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7154	Phase 3
0.6481	Remote Similarity	NPD6373	Approved
0.6481	Remote Similarity	NPD6372	Approved
0.6465	Remote Similarity	NPD8034	Phase 2
0.6465	Remote Similarity	NPD8035	Phase 2
0.6449	Remote Similarity	NPD5697	Approved
0.6449	Remote Similarity	NPD5701	Approved
0.6436	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6883	Approved
0.6422	Remote Similarity	NPD7290	Approved
0.6422	Remote Similarity	NPD7102	Approved
0.6421	Remote Similarity	NPD4786	Approved
0.6421	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7638	Approved
0.6383	Remote Similarity	NPD3667	Approved
0.6383	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6650	Approved
0.6364	Remote Similarity	NPD6649	Approved
0.6364	Remote Similarity	NPD6869	Approved
0.6364	Remote Similarity	NPD6847	Approved
0.6364	Remote Similarity	NPD6617	Approved
0.6364	Remote Similarity	NPD8130	Phase 1
0.6364	Remote Similarity	NPD7838	Discovery
0.6348	Remote Similarity	NPD6319	Approved
0.6346	Remote Similarity	NPD7639	Approved
0.6346	Remote Similarity	NPD7640	Approved
0.6344	Remote Similarity	NPD5368	Approved
0.633	Remote Similarity	NPD6014	Approved
0.633	Remote Similarity	NPD6012	Approved
0.633	Remote Similarity	NPD6013	Approved
0.6325	Remote Similarity	NPD8328	Phase 3
0.6316	Remote Similarity	NPD6695	Phase 3
0.6306	Remote Similarity	NPD6053	Discontinued
0.6306	Remote Similarity	NPD8297	Approved
0.6306	Remote Similarity	NPD6882	Approved
0.6304	Remote Similarity	NPD4238	Approved
0.6304	Remote Similarity	NPD4802	Phase 2
0.6304	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.63	Remote Similarity	NPD5281	Approved
0.63	Remote Similarity	NPD5284	Approved
0.6296	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6422	Discontinued
0.6289	Remote Similarity	NPD6098	Approved
0.6275	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7492	Approved
0.6263	Remote Similarity	NPD4753	Phase 2
0.6263	Remote Similarity	NPD1695	Approved
0.6263	Remote Similarity	NPD6080	Approved
0.6263	Remote Similarity	NPD6904	Approved
0.6263	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6673	Approved
0.625	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD3133	Approved
0.625	Remote Similarity	NPD3665	Phase 1
0.6239	Remote Similarity	NPD6011	Approved
0.6228	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD7632	Discontinued
0.6224	Remote Similarity	NPD3573	Approved
0.6218	Remote Similarity	NPD6616	Approved
0.6216	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4270	Approved
0.6211	Remote Similarity	NPD4269	Approved
0.6207	Remote Similarity	NPD6054	Approved
0.6207	Remote Similarity	NPD6059	Approved
0.6203	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5785	Approved
0.6186	Remote Similarity	NPD1694	Approved
0.6186	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4822	Approved
0.617	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4695	Discontinued
0.617	Remote Similarity	NPD4820	Approved
0.617	Remote Similarity	NPD4819	Approved
0.617	Remote Similarity	NPD4821	Approved
0.6167	Remote Similarity	NPD7078	Approved
0.6167	Remote Similarity	NPD8293	Discontinued
0.6163	Remote Similarity	NPD7331	Phase 2
0.6154	Remote Similarity	NPD4755	Approved
0.6154	Remote Similarity	NPD3702	Approved
0.6146	Remote Similarity	NPD5362	Discontinued
0.6139	Remote Similarity	NPD6050	Approved
0.6132	Remote Similarity	NPD5344	Discontinued
0.6129	Remote Similarity	NPD3617	Approved
0.6129	Remote Similarity	NPD6118	Approved
0.6129	Remote Similarity	NPD6115	Approved
0.6129	Remote Similarity	NPD6697	Approved
0.6129	Remote Similarity	NPD6114	Approved
0.6126	Remote Similarity	NPD4634	Approved
0.6122	Remote Similarity	NPD3618	Phase 1
0.6122	Remote Similarity	NPD5786	Approved
0.6122	Remote Similarity	NPD5279	Phase 3
0.6116	Remote Similarity	NPD7736	Approved
0.6106	Remote Similarity	NPD8133	Approved
0.6106	Remote Similarity	NPD4632	Approved
0.6105	Remote Similarity	NPD4139	Approved
0.6105	Remote Similarity	NPD4692	Approved
0.6102	Remote Similarity	NPD6370	Approved
0.61	Remote Similarity	NPD5328	Approved
0.6095	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD3668	Phase 3
0.6082	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD4202	Approved
0.6066	Remote Similarity	NPD7319	Approved
0.6061	Remote Similarity	NPD7524	Approved
0.6061	Remote Similarity	NPD7750	Discontinued
0.6061	Remote Similarity	NPD4251	Approved
0.6061	Remote Similarity	NPD4250	Approved
0.605	Remote Similarity	NPD7604	Phase 2
0.6042	Remote Similarity	NPD4221	Approved
0.6042	Remote Similarity	NPD4223	Phase 3
0.604	Remote Similarity	NPD5692	Phase 3
0.6038	Remote Similarity	NPD5285	Approved
0.6038	Remote Similarity	NPD4696	Approved
0.6038	Remote Similarity	NPD6648	Approved
0.6038	Remote Similarity	NPD5286	Approved
0.6038	Remote Similarity	NPD4700	Approved
0.6022	Remote Similarity	NPD6116	Phase 1
0.602	Remote Similarity	NPD5363	Approved
0.602	Remote Similarity	NPD5329	Approved
0.6017	Remote Similarity	NPD8517	Approved
0.6017	Remote Similarity	NPD6016	Approved
0.6017	Remote Similarity	NPD8516	Approved
0.6017	Remote Similarity	NPD8515	Approved
0.6017	Remote Similarity	NPD6015	Approved
0.6017	Remote Similarity	NPD8513	Phase 3
0.6017	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD5208	Approved
0.6	Remote Similarity	NPD4252	Approved
0.6	Remote Similarity	NPD6930	Phase 2
0.6	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6931	Approved
0.5983	Remote Similarity	NPD7101	Approved
0.5983	Remote Similarity	NPD7100	Approved
0.598	Remote Similarity	NPD5693	Phase 1
0.598	Remote Similarity	NPD5694	Approved
0.598	Remote Similarity	NPD6079	Approved
0.5966	Remote Similarity	NPD8080	Discontinued
0.5966	Remote Similarity	NPD5988	Approved
0.5962	Remote Similarity	NPD5210	Approved
0.5962	Remote Similarity	NPD4629	Approved
0.596	Remote Similarity	NPD4249	Approved
0.5957	Remote Similarity	NPD4271	Approved

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