NPASS Compound

Structure

NPC471372 OpenBabel07101718332D 34 36 0 0 1 0 0 0 0 0999 V2000 -6.7471 1.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9502 0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7741 2.7387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6978 -0.4060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5153 3.9723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6201 -2.9928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3417 1.8960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5153 0.0804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7741 1.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9985 0.3681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3146 1.8960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8281 1.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0126 -0.4060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3273 2.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0126 2.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2876 1.8960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8552 0.0804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3273 4.4588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9691 -2.2698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1699 2.9994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3273 1.5399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0126 1.5399 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1699 0.0804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3957 0.8889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9676 0.1017 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8552 1.0534 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1699 1.0534 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3273 5.4318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0174 -2.4721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3273 -0.4060 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3475 1.0911 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1699 3.9723 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2697 -1.3444 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 9 2 0 0 0 0 2 10 1 0 0 0 0 3 16 2 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 8 30 1 0 0 0 0 9 16 1 0 0 0 0 10 31 1 0 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 12 26 1 0 0 0 0 13 17 1 0 0 0 0 13 23 1 0 0 0 0 14 20 1 0 0 0 0 14 21 2 0 0 0 0 15 20 1 0 0 0 0 15 22 1 0 0 0 0 17 26 1 6 0 0 0 18 28 2 0 0 0 0 18 32 1 0 0 0 0 19 29 2 0 0 0 0 19 33 1 0 0 0 0 20 32 1 1 0 0 0 21 24 1 0 0 0 0 22 26 1 1 0 0 0 22 27 1 0 0 0 0 23 27 1 6 0 0 0 23 30 1 0 0 0 0 24 31 1 1 0 0 0 24 34 1 0 0 0 0 25 27 1 6 0 0 0 25 33 1 0 0 0 0 25 34 1 0 0 0 0 26 7 1 1 0 0 0 27 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.28
Volume:	498.228
LogP:	3.487
LogD:	3.062
LogS:	-4.489
# Rotatable Bonds:	11
TPSA:	80.29
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	5.767
Fsp3:	0.704
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:	-4.754
MDCK Permeability:	2.610826959426049e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	74.01467895507812%
Volume Distribution (VD):	2.063
Pgp-substrate:	31.36962127685547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.497
CYP2C9-inhibitor:	0.054
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.532
CYP3A4-substrate:	0.453

ADMET: Excretion

Clearance (CL):	3.17
Half-life (T1/2):	0.353

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.947
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.606
Rat Oral Acute Toxicity:	0.139
Maximum Recommended Daily Dose:	0.774
Skin Sensitization:	0.809
Carcinogencity:	0.095
Eye Corrosion:	0.014
Eye Irritation:	0.043
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC471372

Natural Product ID:	NPC471372
*Common Name:**	Rel-(2R,5R,6R,8S,9S,10R,18S,19R)-2,19-Diacetoxy-18-Ethoxy-6-Methoxycleroda-3,13(16),14-Trien-18,19-Oxolane
IUPAC Name:	[(1R,3S,5R,6aR,7S,8S,10R,10aR)-1-acetyloxy-3-ethoxy-10-methoxy-7,8-dimethyl-7-(3-methylidenepent-4-enyl)-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] acetate
Synonyms:
Standard InCHIKey:	TWFKTSOJWWQSLG-XWOLWVNESA-N
Standard InCHI:	InChI=1S/C27H40O7/c1-9-16(3)11-12-26(7)17(4)13-23(30-8)27-21(14-20(15-22(26)27)32-18(5)28)24(31-10-2)34-25(27)33-19(6)29/h9,14,17,20,22-25H,1,3,10-13,15H2,2,4-8H3/t17-,20-,22+,23+,24-,25-,26-,27-/m0/s1
SMILES:	CCO[C@H]1O[C@@H]([C@]23C1=C[C@H](OC(=O)C)C[C@@H]3[C@@]([C@H](C[C@H]2OC)C)(C)CCC(=C)C=C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419882
PubChem CID:	73346139
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[24033131]
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	twigs	n.a.	n.a.	PMID[25286284]
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26699618]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	=	55700.0	nM	PMID[527906]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	53300.0	nM	PMID[527906]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	35900.0	nM	PMID[527906]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	47200.0	nM	PMID[527906]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	34200.0	nM	PMID[527906]

☑ 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 NPC471372 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	213
0.1-0.2	1258
0.2-0.3	4528
0.3-0.4	10275
0.4-0.5	11898
0.5-0.6	7629
0.6-0.7	5684
0.7-0.8	1077
0.8-0.85	36
0.85-0.9	43
0.9-0.95	36
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471362
1.0	High Similarity	NPC472189
0.9888	High Similarity	NPC171598
0.9778	High Similarity	NPC472188
0.967	High Similarity	NPC472186
0.967	High Similarity	NPC476800
0.967	High Similarity	NPC471366
0.967	High Similarity	NPC318917
0.9565	High Similarity	NPC473204
0.9565	High Similarity	NPC473545
0.9565	High Similarity	NPC472187
0.9362	High Similarity	NPC471363
0.9362	High Similarity	NPC238397
0.9263	High Similarity	NPC475889
0.9263	High Similarity	NPC127933
0.9263	High Similarity	NPC7644
0.9263	High Similarity	NPC134270
0.9263	High Similarity	NPC7613
0.9239	High Similarity	NPC94905
0.9239	High Similarity	NPC8954
0.9231	High Similarity	NPC88507
0.9167	High Similarity	NPC264867
0.9167	High Similarity	NPC470321
0.9167	High Similarity	NPC201880
0.9167	High Similarity	NPC473207
0.9167	High Similarity	NPC81567
0.9072	High Similarity	NPC252296
0.9032	High Similarity	NPC311166
0.898	High Similarity	NPC88013
0.898	High Similarity	NPC125423
0.898	High Similarity	NPC184512
0.898	High Similarity	NPC109376
0.8936	High Similarity	NPC98112
0.8889	High Similarity	NPC224660
0.8889	High Similarity	NPC470024
0.8889	High Similarity	NPC48548
0.8889	High Similarity	NPC128795
0.8889	High Similarity	NPC311223
0.8889	High Similarity	NPC135015
0.8889	High Similarity	NPC217921
0.8878	High Similarity	NPC172867
0.88	High Similarity	NPC40728
0.88	High Similarity	NPC316974
0.875	High Similarity	NPC228251
0.875	High Similarity	NPC219285
0.875	High Similarity	NPC477972
0.875	High Similarity	NPC477971
0.875	High Similarity	NPC161527
0.875	High Similarity	NPC20113
0.875	High Similarity	NPC477968
0.8713	High Similarity	NPC119550
0.8713	High Similarity	NPC316708
0.8687	High Similarity	NPC218158
0.8673	High Similarity	NPC471365
0.8673	High Similarity	NPC120009
0.8673	High Similarity	NPC471364
0.8673	High Similarity	NPC132395
0.8652	High Similarity	NPC471367
0.8627	High Similarity	NPC470026
0.8627	High Similarity	NPC17791
0.8587	High Similarity	NPC293044
0.8587	High Similarity	NPC470819
0.8544	High Similarity	NPC317460
0.8544	High Similarity	NPC328074
0.8544	High Similarity	NPC321272
0.8544	High Similarity	NPC470025
0.8495	Intermediate Similarity	NPC470817
0.8462	Intermediate Similarity	NPC471368
0.8462	Intermediate Similarity	NPC470027
0.8462	Intermediate Similarity	NPC102996
0.8462	Intermediate Similarity	NPC471369
0.837	Intermediate Similarity	NPC102640
0.8333	Intermediate Similarity	NPC100892
0.8333	Intermediate Similarity	NPC477969
0.8333	Intermediate Similarity	NPC135224
0.8333	Intermediate Similarity	NPC477970
0.8298	Intermediate Similarity	NPC469403
0.828	Intermediate Similarity	NPC263079
0.828	Intermediate Similarity	NPC69713
0.8261	Intermediate Similarity	NPC323209
0.8261	Intermediate Similarity	NPC118266
0.8252	Intermediate Similarity	NPC112457
0.8252	Intermediate Similarity	NPC206618
0.8235	Intermediate Similarity	NPC475074
0.8229	Intermediate Similarity	NPC477722
0.8229	Intermediate Similarity	NPC189513
0.8202	Intermediate Similarity	NPC473685
0.8202	Intermediate Similarity	NPC469802
0.8191	Intermediate Similarity	NPC261320
0.8191	Intermediate Similarity	NPC246028
0.8182	Intermediate Similarity	NPC324841
0.8163	Intermediate Similarity	NPC125551
0.8163	Intermediate Similarity	NPC239547
0.8163	Intermediate Similarity	NPC91197
0.8163	Intermediate Similarity	NPC309503
0.8163	Intermediate Similarity	NPC96597
0.8163	Intermediate Similarity	NPC155319
0.8155	Intermediate Similarity	NPC38948
0.8152	Intermediate Similarity	NPC472442
0.8144	Intermediate Similarity	NPC230347
0.8144	Intermediate Similarity	NPC286612
0.8144	Intermediate Similarity	NPC275310
0.8132	Intermediate Similarity	NPC472440
0.8125	Intermediate Similarity	NPC163902
0.8125	Intermediate Similarity	NPC12297
0.8119	Intermediate Similarity	NPC45897
0.8119	Intermediate Similarity	NPC471887
0.8119	Intermediate Similarity	NPC471888
0.8119	Intermediate Similarity	NPC471886
0.8119	Intermediate Similarity	NPC471885
0.8119	Intermediate Similarity	NPC471450
0.8111	Intermediate Similarity	NPC25554
0.8105	Intermediate Similarity	NPC471371
0.8105	Intermediate Similarity	NPC220216
0.8105	Intermediate Similarity	NPC471370
0.81	Intermediate Similarity	NPC280991
0.8085	Intermediate Similarity	NPC473879
0.8085	Intermediate Similarity	NPC477128
0.8085	Intermediate Similarity	NPC106332
0.8081	Intermediate Similarity	NPC474440
0.8081	Intermediate Similarity	NPC473154
0.8061	Intermediate Similarity	NPC165632
0.8058	Intermediate Similarity	NPC472390
0.8041	Intermediate Similarity	NPC140277
0.8039	Intermediate Similarity	NPC222161
0.8039	Intermediate Similarity	NPC470768
0.8022	Intermediate Similarity	NPC471218
0.8021	Intermediate Similarity	NPC124374
0.8021	Intermediate Similarity	NPC474631
0.8021	Intermediate Similarity	NPC477574
0.802	Intermediate Similarity	NPC300399
0.802	Intermediate Similarity	NPC471889
0.802	Intermediate Similarity	NPC471482
0.802	Intermediate Similarity	NPC11956
0.802	Intermediate Similarity	NPC37207
0.802	Intermediate Similarity	NPC470571
0.8019	Intermediate Similarity	NPC473125
0.8	Intermediate Similarity	NPC473219
0.8	Intermediate Similarity	NPC470761
0.7979	Intermediate Similarity	NPC471779
0.7979	Intermediate Similarity	NPC166857
0.7961	Intermediate Similarity	NPC82251
0.7961	Intermediate Similarity	NPC470763
0.7961	Intermediate Similarity	NPC470767
0.7961	Intermediate Similarity	NPC239961
0.7959	Intermediate Similarity	NPC276110
0.7957	Intermediate Similarity	NPC119001
0.7944	Intermediate Similarity	NPC49413
0.7944	Intermediate Similarity	NPC40133
0.7944	Intermediate Similarity	NPC44298
0.7944	Intermediate Similarity	NPC157441
0.7944	Intermediate Similarity	NPC473128
0.7944	Intermediate Similarity	NPC290608
0.7941	Intermediate Similarity	NPC23584
0.7938	Intermediate Similarity	NPC99653
0.7938	Intermediate Similarity	NPC7349
0.7938	Intermediate Similarity	NPC472812
0.7921	Intermediate Similarity	NPC198992
0.7921	Intermediate Similarity	NPC472554
0.7921	Intermediate Similarity	NPC475767
0.7921	Intermediate Similarity	NPC119467
0.7921	Intermediate Similarity	NPC475617
0.79	Intermediate Similarity	NPC477928
0.7895	Intermediate Similarity	NPC93411
0.7885	Intermediate Similarity	NPC293512
0.7879	Intermediate Similarity	NPC475380
0.7879	Intermediate Similarity	NPC211810
0.7879	Intermediate Similarity	NPC221801
0.7879	Intermediate Similarity	NPC471765
0.7879	Intermediate Similarity	NPC73858
0.7879	Intermediate Similarity	NPC194132
0.7879	Intermediate Similarity	NPC284194
0.7879	Intermediate Similarity	NPC112654
0.7879	Intermediate Similarity	NPC209297
0.7872	Intermediate Similarity	NPC286153
0.7864	Intermediate Similarity	NPC31430
0.7864	Intermediate Similarity	NPC85593
0.7857	Intermediate Similarity	NPC104925
0.7857	Intermediate Similarity	NPC477129
0.7857	Intermediate Similarity	NPC298973
0.7857	Intermediate Similarity	NPC105490
0.7857	Intermediate Similarity	NPC96736
0.7857	Intermediate Similarity	NPC477130
0.7857	Intermediate Similarity	NPC472360
0.7857	Intermediate Similarity	NPC472416
0.7857	Intermediate Similarity	NPC178949
0.7857	Intermediate Similarity	NPC211238
0.7857	Intermediate Similarity	NPC470255
0.785	Intermediate Similarity	NPC194951
0.785	Intermediate Similarity	NPC12046
0.7849	Intermediate Similarity	NPC96055
0.7843	Intermediate Similarity	NPC472815
0.7843	Intermediate Similarity	NPC472552
0.7843	Intermediate Similarity	NPC476471
0.7843	Intermediate Similarity	NPC475344
0.7843	Intermediate Similarity	NPC154452
0.7835	Intermediate Similarity	NPC65513
0.7835	Intermediate Similarity	NPC472811
0.7835	Intermediate Similarity	NPC234335
0.783	Intermediate Similarity	NPC177047

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 NPC471372 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1472
0.2-0.3	3938
0.3-0.4	2355
0.4-0.5	766
0.5-0.6	294
0.6-0.7	143
0.7-0.8	9
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
0.7456	Intermediate Similarity	NPD7503	Approved
0.7379	Intermediate Similarity	NPD7638	Approved
0.7345	Intermediate Similarity	NPD7328	Approved
0.7345	Intermediate Similarity	NPD7327	Approved
0.7315	Intermediate Similarity	NPD6686	Approved
0.7308	Intermediate Similarity	NPD7640	Approved
0.7308	Intermediate Similarity	NPD7639	Approved
0.7304	Intermediate Similarity	NPD8033	Approved
0.7281	Intermediate Similarity	NPD7516	Approved
0.7217	Intermediate Similarity	NPD8377	Approved
0.7217	Intermediate Similarity	NPD8294	Approved
0.7155	Intermediate Similarity	NPD8296	Approved
0.7155	Intermediate Similarity	NPD8335	Approved
0.7155	Intermediate Similarity	NPD8380	Approved
0.7155	Intermediate Similarity	NPD8379	Approved
0.7155	Intermediate Similarity	NPD8378	Approved
0.7143	Intermediate Similarity	NPD6648	Approved
0.7113	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6051	Approved
0.7048	Intermediate Similarity	NPD4225	Approved
0.7041	Intermediate Similarity	NPD1694	Approved
0.7009	Intermediate Similarity	NPD8517	Approved
0.7009	Intermediate Similarity	NPD8515	Approved
0.7009	Intermediate Similarity	NPD8516	Approved
0.7009	Intermediate Similarity	NPD8513	Phase 3
0.6917	Remote Similarity	NPD7507	Approved
0.6916	Remote Similarity	NPD5344	Discontinued
0.6818	Remote Similarity	NPD6008	Approved
0.6796	Remote Similarity	NPD7637	Suspended
0.6786	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6412	Phase 2
0.6757	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7319	Approved
0.6735	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6399	Phase 3
0.6731	Remote Similarity	NPD5778	Approved
0.6731	Remote Similarity	NPD5779	Approved
0.6697	Remote Similarity	NPD7632	Discontinued
0.6696	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6637	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6882	Approved
0.66	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD8293	Discontinued
0.6579	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7492	Approved
0.6538	Remote Similarity	NPD7838	Discovery
0.6526	Remote Similarity	NPD8039	Approved
0.6525	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD7115	Discovery
0.6517	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7748	Approved
0.6504	Remote Similarity	NPD6616	Approved
0.65	Remote Similarity	NPD6695	Phase 3
0.65	Remote Similarity	NPD6054	Approved
0.6481	Remote Similarity	NPD7902	Approved
0.6476	Remote Similarity	NPD6411	Approved
0.6475	Remote Similarity	NPD8328	Phase 3
0.6471	Remote Similarity	NPD7146	Approved
0.6471	Remote Similarity	NPD5330	Approved
0.6471	Remote Similarity	NPD6684	Approved
0.6471	Remote Similarity	NPD7521	Approved
0.6471	Remote Similarity	NPD7334	Approved
0.6471	Remote Similarity	NPD6409	Approved
0.6452	Remote Similarity	NPD8074	Phase 3
0.6452	Remote Similarity	NPD7078	Approved
0.6429	Remote Similarity	NPD7645	Phase 2
0.6404	Remote Similarity	NPD6881	Approved
0.6404	Remote Similarity	NPD6899	Approved
0.6387	Remote Similarity	NPD6009	Approved
0.6379	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7128	Approved
0.6372	Remote Similarity	NPD5739	Approved
0.6372	Remote Similarity	NPD6402	Approved
0.6372	Remote Similarity	NPD6675	Approved
0.6364	Remote Similarity	NPD6059	Approved
0.6364	Remote Similarity	NPD7525	Registered
0.6354	Remote Similarity	NPD8264	Approved
0.6346	Remote Similarity	NPD5737	Approved
0.6346	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6672	Approved
0.6346	Remote Similarity	NPD6903	Approved
0.6341	Remote Similarity	NPD6067	Discontinued
0.6325	Remote Similarity	NPD6053	Discontinued
0.6321	Remote Similarity	NPD7515	Phase 2
0.6316	Remote Similarity	NPD5697	Approved
0.6311	Remote Similarity	NPD6015	Approved
0.6311	Remote Similarity	NPD6016	Approved
0.6296	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7290	Approved
0.6293	Remote Similarity	NPD7102	Approved
0.6293	Remote Similarity	NPD6883	Approved
0.6286	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6101	Approved
0.6263	Remote Similarity	NPD6929	Approved
0.6261	Remote Similarity	NPD7320	Approved
0.6261	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5988	Approved
0.625	Remote Similarity	NPD4250	Approved
0.625	Remote Similarity	NPD4251	Approved
0.625	Remote Similarity	NPD7750	Discontinued
0.625	Remote Similarity	NPD7524	Approved
0.625	Remote Similarity	NPD3573	Approved
0.6239	Remote Similarity	NPD6617	Approved
0.6239	Remote Similarity	NPD8130	Phase 1
0.6239	Remote Similarity	NPD6847	Approved
0.6239	Remote Similarity	NPD6650	Approved
0.6239	Remote Similarity	NPD6649	Approved
0.6239	Remote Similarity	NPD6869	Approved
0.6226	Remote Similarity	NPD3168	Discontinued
0.6226	Remote Similarity	NPD6698	Approved
0.6226	Remote Similarity	NPD46	Approved
0.6207	Remote Similarity	NPD6373	Approved
0.6207	Remote Similarity	NPD6372	Approved
0.6207	Remote Similarity	NPD6014	Approved
0.6207	Remote Similarity	NPD6013	Approved
0.6207	Remote Similarity	NPD6012	Approved
0.62	Remote Similarity	NPD7514	Phase 3
0.62	Remote Similarity	NPD7332	Phase 2
0.62	Remote Similarity	NPD6930	Phase 2
0.62	Remote Similarity	NPD6931	Approved
0.6186	Remote Similarity	NPD7339	Approved
0.6186	Remote Similarity	NPD6942	Approved
0.6186	Remote Similarity	NPD8297	Approved
0.6174	Remote Similarity	NPD5701	Approved
0.6168	Remote Similarity	NPD5693	Phase 1
0.6168	Remote Similarity	NPD8035	Phase 2
0.6168	Remote Similarity	NPD8034	Phase 2
0.6162	Remote Similarity	NPD7145	Approved
0.6154	Remote Similarity	NPD4249	Approved
0.6139	Remote Similarity	NPD6902	Approved
0.6134	Remote Similarity	NPD4632	Approved
0.6132	Remote Similarity	NPD1695	Approved
0.6122	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6011	Approved
0.6117	Remote Similarity	NPD4786	Approved
0.6117	Remote Similarity	NPD3668	Phase 3
0.6098	Remote Similarity	NPD6319	Approved
0.6095	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5209	Approved
0.6078	Remote Similarity	NPD3667	Approved
0.6075	Remote Similarity	NPD5207	Approved
0.6061	Remote Similarity	NPD5776	Phase 2
0.6061	Remote Similarity	NPD6932	Approved
0.6061	Remote Similarity	NPD6925	Approved
0.604	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6084	Phase 2
0.6036	Remote Similarity	NPD6083	Phase 2
0.6019	Remote Similarity	NPD6050	Approved
0.6019	Remote Similarity	NPD7983	Approved
0.6019	Remote Similarity	NPD7087	Discontinued
0.6019	Remote Similarity	NPD6079	Approved
0.6019	Remote Similarity	NPD5694	Approved
0.6	Remote Similarity	NPD6098	Approved
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7260	Phase 2
0.5981	Remote Similarity	NPD5328	Approved
0.5981	Remote Similarity	NPD6080	Approved
0.5981	Remote Similarity	NPD6904	Approved
0.5981	Remote Similarity	NPD6673	Approved
0.5966	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5211	Phase 2
0.5952	Remote Similarity	NPD7604	Phase 2
0.5946	Remote Similarity	NPD7839	Suspended
0.5929	Remote Similarity	NPD5285	Approved
0.5929	Remote Similarity	NPD5286	Approved
0.5929	Remote Similarity	NPD4696	Approved
0.5926	Remote Similarity	NPD5692	Phase 3
0.592	Remote Similarity	NPD5983	Phase 2
0.5918	Remote Similarity	NPD6924	Approved
0.5918	Remote Similarity	NPD6926	Approved
0.5914	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5282	Discontinued
0.5909	Remote Similarity	NPD6001	Approved
0.5905	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6893	Approved
0.5905	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD4755	Approved
0.5891	Remote Similarity	NPD6033	Approved
0.5887	Remote Similarity	NPD7100	Approved
0.5887	Remote Similarity	NPD7101	Approved
0.5882	Remote Similarity	NPD4819	Approved
0.5882	Remote Similarity	NPD7509	Discontinued
0.5882	Remote Similarity	NPD4822	Approved
0.5882	Remote Similarity	NPD4820	Approved
0.5882	Remote Similarity	NPD6371	Approved
0.5882	Remote Similarity	NPD4821	Approved
0.5876	Remote Similarity	NPD7150	Approved
0.5876	Remote Similarity	NPD7152	Approved
0.5876	Remote Similarity	NPD7151	Approved
0.5873	Remote Similarity	NPD5125	Phase 3
0.5873	Remote Similarity	NPD5126	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