NPASS Compound

Structure

NPC263079 OpenBabel07101719522D 30 32 0 0 1 0 0 0 0 0999 V2000 -6.7243 1.0499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7547 2.7294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6853 -0.4047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6921 -0.5554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6113 -2.9828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3304 1.8896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7547 1.0499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3001 1.8896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0058 -0.4047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8153 1.0499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1660 0.0802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3262 2.5044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0058 2.5044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2698 1.8896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8456 0.0802 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9918 0.3668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9624 -2.2621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1660 2.9893 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3262 1.5347 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0058 1.5347 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3944 0.8859 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9644 0.1014 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8456 1.0499 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1660 1.0499 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9403 0.5685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0139 -2.4637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1660 3.9590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3429 1.0875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2621 -1.3399 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 7 2 0 0 0 0 2 14 2 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 23 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 15 23 1 1 0 0 0 16 25 2 0 0 0 0 16 28 1 0 0 0 0 17 26 2 0 0 0 0 17 29 1 0 0 0 0 18 27 1 1 0 0 0 19 21 1 0 0 0 0 19 24 1 1 0 0 0 20 23 1 6 0 0 0 20 24 1 0 0 0 0 21 28 1 1 0 0 0 21 30 1 0 0 0 0 22 24 1 6 0 0 0 22 29 1 0 0 0 0 22 30 1 0 0 0 0 23 6 1 6 0 0 0 24 11 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.25
Volume:	440.186
LogP:	3.742
LogD:	3.059
LogS:	-4.869
# Rotatable Bonds:	8
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.514
Synthetic Accessibility Score:	5.609
Fsp3:	0.75
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:	-4.821
MDCK Permeability:	2.2940850612940267e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.901
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.225
Plasma Protein Binding (PPB):	64.52941131591797%
Volume Distribution (VD):	1.701
Pgp-substrate:	43.469722747802734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.075
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.417
CYP2C9-inhibitor:	0.07
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.19
CYP3A4-inhibitor:	0.398
CYP3A4-substrate:	0.367

ADMET: Excretion

Clearance (CL):	2.524
Half-life (T1/2):	0.376

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.335
Drug-inuced Liver Injury (DILI):	0.75
AMES Toxicity:	0.807
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.937
Carcinogencity:	0.367
Eye Corrosion:	0.258
Eye Irritation:	0.276
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC263079

Natural Product ID:	NPC263079
*Common Name:**	Rel-(2R,4R,5S,8R,9R,10S,18R,19R)-18,19-Diacetoxy-18,19-Epoxycleroda-3(16),14-Dien-2-Ol
IUPAC Name:	[(1R,3R,3aR,5R,6aS,7R,8R,10aS)-1-acetyloxy-5-hydroxy-7,8-dimethyl-7-(3-methylidenepent-4-enyl)-1,3,3a,4,5,6,6a,8,9,10-decahydrobenzo[d][2]benzofuran-3-yl] acetate
Synonyms:
Standard InCHIKey:	CCKRIICYFGYUQF-UXROZCACSA-N
Standard InCHI:	InChI=1S/C24H36O6/c1-7-14(2)8-10-23(6)15(3)9-11-24-19(12-18(27)13-20(23)24)21(28-16(4)25)30-22(24)29-17(5)26/h7,15,18-22,27H,1-2,8-13H2,3-6H3/t15-,18+,19+,20+,21+,22+,23-,24-/m1/s1
SMILES:	C=CC(=C)CC[C@]1(C)[C@H](C)CC[C@@]23[C@@H](C[C@@H](C[C@@H]12)O)[C@@H](OC(=O)C)O[C@@H]3OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419874
PubChem CID:	14705633
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	=	26300.0	nM	PMID[508025]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	15200.0	nM	PMID[508025]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	17900.0	nM	PMID[508025]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	6600.0	nM	PMID[508025]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	8200.0	nM	PMID[508025]

☑ 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 NPC263079 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	167
0.1-0.2	1289
0.2-0.3	5350
0.3-0.4	14613
0.4-0.5	8094
0.5-0.6	5669
0.6-0.7	6146
0.7-0.8	1273
0.8-0.85	87
0.85-0.9	5
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9762	High Similarity	NPC471371
0.9762	High Similarity	NPC471370
0.9512	High Similarity	NPC471367
0.9286	High Similarity	NPC471369
0.9059	High Similarity	NPC471368
0.8526	High Similarity	NPC471363
0.8526	High Similarity	NPC238397
0.8495	Intermediate Similarity	NPC471770
0.8495	Intermediate Similarity	NPC473555
0.8495	Intermediate Similarity	NPC278939
0.8495	Intermediate Similarity	NPC98112
0.8478	Intermediate Similarity	NPC275310
0.8478	Intermediate Similarity	NPC230347
0.8478	Intermediate Similarity	NPC286612
0.8454	Intermediate Similarity	NPC218158
0.8438	Intermediate Similarity	NPC134270
0.8438	Intermediate Similarity	NPC127933
0.8438	Intermediate Similarity	NPC7644
0.8438	Intermediate Similarity	NPC7613
0.8438	Intermediate Similarity	NPC475889
0.8404	Intermediate Similarity	NPC157739
0.837	Intermediate Similarity	NPC211238
0.8351	Intermediate Similarity	NPC81567
0.8351	Intermediate Similarity	NPC473207
0.8351	Intermediate Similarity	NPC201880
0.8351	Intermediate Similarity	NPC470321
0.8351	Intermediate Similarity	NPC264867
0.8316	Intermediate Similarity	NPC20113
0.8316	Intermediate Similarity	NPC228251
0.8316	Intermediate Similarity	NPC477971
0.8316	Intermediate Similarity	NPC477972
0.8316	Intermediate Similarity	NPC477968
0.8316	Intermediate Similarity	NPC161527
0.8316	Intermediate Similarity	NPC219285
0.8316	Intermediate Similarity	NPC317019
0.8298	Intermediate Similarity	NPC97867
0.8295	Intermediate Similarity	NPC164424
0.828	Intermediate Similarity	NPC472189
0.828	Intermediate Similarity	NPC471372
0.828	Intermediate Similarity	NPC471362
0.8265	Intermediate Similarity	NPC172867
0.8265	Intermediate Similarity	NPC252296
0.8261	Intermediate Similarity	NPC12297
0.8261	Intermediate Similarity	NPC474835
0.8191	Intermediate Similarity	NPC171598
0.8182	Intermediate Similarity	NPC88013
0.8182	Intermediate Similarity	NPC299963
0.8182	Intermediate Similarity	NPC109376
0.8182	Intermediate Similarity	NPC184512
0.8182	Intermediate Similarity	NPC102048
0.8182	Intermediate Similarity	NPC125423
0.8163	Intermediate Similarity	NPC31430
0.8163	Intermediate Similarity	NPC85593
0.8161	Intermediate Similarity	NPC472504
0.8152	Intermediate Similarity	NPC120539
0.8144	Intermediate Similarity	NPC154452
0.8144	Intermediate Similarity	NPC470571
0.8132	Intermediate Similarity	NPC473058
0.8125	Intermediate Similarity	NPC324841
0.8125	Intermediate Similarity	NPC146188
0.8105	Intermediate Similarity	NPC472188
0.81	Intermediate Similarity	NPC217921
0.81	Intermediate Similarity	NPC48548
0.81	Intermediate Similarity	NPC224660
0.81	Intermediate Similarity	NPC311223
0.81	Intermediate Similarity	NPC135015
0.81	Intermediate Similarity	NPC128795
0.81	Intermediate Similarity	NPC470024
0.8081	Intermediate Similarity	NPC470056
0.8081	Intermediate Similarity	NPC470055
0.8068	Intermediate Similarity	NPC474253
0.8068	Intermediate Similarity	NPC474346
0.8068	Intermediate Similarity	NPC475820
0.8068	Intermediate Similarity	NPC474284
0.8068	Intermediate Similarity	NPC213737
0.8065	Intermediate Similarity	NPC246860
0.8061	Intermediate Similarity	NPC120009
0.8043	Intermediate Similarity	NPC469403
0.8043	Intermediate Similarity	NPC159876
0.8041	Intermediate Similarity	NPC21064
0.8041	Intermediate Similarity	NPC121072
0.8021	Intermediate Similarity	NPC472186
0.8021	Intermediate Similarity	NPC471366
0.8021	Intermediate Similarity	NPC476800
0.8021	Intermediate Similarity	NPC477928
0.8021	Intermediate Similarity	NPC318917
0.802	Intermediate Similarity	NPC316974
0.802	Intermediate Similarity	NPC40728
0.8	Intermediate Similarity	NPC94905
0.8	Intermediate Similarity	NPC8954
0.8	Intermediate Similarity	NPC475074
0.798	Intermediate Similarity	NPC470061
0.798	Intermediate Similarity	NPC470064
0.798	Intermediate Similarity	NPC470058
0.798	Intermediate Similarity	NPC470059
0.798	Intermediate Similarity	NPC470060
0.798	Intermediate Similarity	NPC470057
0.798	Intermediate Similarity	NPC470043
0.798	Intermediate Similarity	NPC470062
0.7979	Intermediate Similarity	NPC178949
0.7979	Intermediate Similarity	NPC96736
0.7979	Intermediate Similarity	NPC305160
0.7979	Intermediate Similarity	NPC88507
0.7957	Intermediate Similarity	NPC48463
0.7955	Intermediate Similarity	NPC2096
0.7955	Intermediate Similarity	NPC208912
0.7941	Intermediate Similarity	NPC316708
0.7941	Intermediate Similarity	NPC119550
0.7938	Intermediate Similarity	NPC473204
0.7938	Intermediate Similarity	NPC472187
0.7938	Intermediate Similarity	NPC473545
0.7935	Intermediate Similarity	NPC470819
0.7935	Intermediate Similarity	NPC16265
0.7917	Intermediate Similarity	NPC91197
0.7917	Intermediate Similarity	NPC239547
0.7917	Intermediate Similarity	NPC198549
0.7917	Intermediate Similarity	NPC125551
0.7917	Intermediate Similarity	NPC113976
0.7917	Intermediate Similarity	NPC309503
0.7917	Intermediate Similarity	NPC155319
0.7917	Intermediate Similarity	NPC96597
0.79	Intermediate Similarity	NPC473199
0.7895	Intermediate Similarity	NPC135224
0.7895	Intermediate Similarity	NPC477969
0.7895	Intermediate Similarity	NPC477970
0.7895	Intermediate Similarity	NPC100892
0.7889	Intermediate Similarity	NPC235402
0.7872	Intermediate Similarity	NPC163902
0.7865	Intermediate Similarity	NPC474789
0.7865	Intermediate Similarity	NPC52108
0.7864	Intermediate Similarity	NPC470026
0.7864	Intermediate Similarity	NPC17791
0.7849	Intermediate Similarity	NPC123252
0.7849	Intermediate Similarity	NPC194485
0.7849	Intermediate Similarity	NPC474249
0.7849	Intermediate Similarity	NPC470817
0.7849	Intermediate Similarity	NPC53890
0.7849	Intermediate Similarity	NPC10274
0.7849	Intermediate Similarity	NPC261990
0.7849	Intermediate Similarity	NPC219937
0.7843	Intermediate Similarity	NPC206618
0.7843	Intermediate Similarity	NPC305939
0.7835	Intermediate Similarity	NPC473154
0.7835	Intermediate Similarity	NPC5358
0.7835	Intermediate Similarity	NPC216260
0.7826	Intermediate Similarity	NPC291665
0.7826	Intermediate Similarity	NPC160304
0.7822	Intermediate Similarity	NPC293512
0.7822	Intermediate Similarity	NPC234160
0.7812	Intermediate Similarity	NPC311166
0.7802	Intermediate Similarity	NPC471411
0.7802	Intermediate Similarity	NPC471410
0.78	Intermediate Similarity	NPC173583
0.7789	Intermediate Similarity	NPC105490
0.7789	Intermediate Similarity	NPC189513
0.7789	Intermediate Similarity	NPC470255
0.7788	Intermediate Similarity	NPC321272
0.7788	Intermediate Similarity	NPC317460
0.7788	Intermediate Similarity	NPC470025
0.7788	Intermediate Similarity	NPC328074
0.7778	Intermediate Similarity	NPC18953
0.7778	Intermediate Similarity	NPC319238
0.7778	Intermediate Similarity	NPC97505
0.7767	Intermediate Similarity	NPC101450
0.7767	Intermediate Similarity	NPC86217
0.7766	Intermediate Similarity	NPC219516
0.7766	Intermediate Similarity	NPC130840
0.7755	Intermediate Similarity	NPC324598
0.7755	Intermediate Similarity	NPC477721
0.7755	Intermediate Similarity	NPC477716
0.7745	Intermediate Similarity	NPC230888
0.7745	Intermediate Similarity	NPC38217
0.7745	Intermediate Similarity	NPC472988
0.7745	Intermediate Similarity	NPC38948
0.7727	Intermediate Similarity	NPC473685
0.7723	Intermediate Similarity	NPC470767
0.7723	Intermediate Similarity	NPC470763
0.7723	Intermediate Similarity	NPC165405
0.7723	Intermediate Similarity	NPC239961
0.7714	Intermediate Similarity	NPC470027
0.77	Intermediate Similarity	NPC471888
0.77	Intermediate Similarity	NPC471450
0.77	Intermediate Similarity	NPC45897
0.77	Intermediate Similarity	NPC281378
0.77	Intermediate Similarity	NPC471886
0.77	Intermediate Similarity	NPC471885
0.77	Intermediate Similarity	NPC474575
0.77	Intermediate Similarity	NPC471887
0.7692	Intermediate Similarity	NPC476602
0.7684	Intermediate Similarity	NPC470656
0.7684	Intermediate Similarity	NPC7349
0.7684	Intermediate Similarity	NPC277721
0.7684	Intermediate Similarity	NPC26046
0.7684	Intermediate Similarity	NPC267266
0.7677	Intermediate Similarity	NPC198992
0.7677	Intermediate Similarity	NPC267510
0.7677	Intermediate Similarity	NPC477717
0.7674	Intermediate Similarity	NPC63958
0.767	Intermediate Similarity	NPC51925
0.767	Intermediate Similarity	NPC296761

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 NPC263079 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1635
0.2-0.3	4225
0.3-0.4	2158
0.4-0.5	511
0.5-0.6	262
0.6-0.7	203
0.7-0.8	14
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
0.73	Intermediate Similarity	NPD7638	Approved
0.7238	Intermediate Similarity	NPD6686	Approved
0.7228	Intermediate Similarity	NPD7640	Approved
0.7228	Intermediate Similarity	NPD7639	Approved
0.7222	Intermediate Similarity	NPD8133	Approved
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.7117	Intermediate Similarity	NPD7327	Approved
0.7117	Intermediate Similarity	NPD7328	Approved
0.708	Intermediate Similarity	NPD7503	Approved
0.7054	Intermediate Similarity	NPD7516	Approved
0.7041	Intermediate Similarity	NPD8035	Phase 2
0.7041	Intermediate Similarity	NPD8034	Phase 2
0.7009	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD8377	Approved
0.6991	Remote Similarity	NPD8294	Approved
0.697	Remote Similarity	NPD6399	Phase 3
0.6957	Remote Similarity	NPD7525	Registered
0.6957	Remote Similarity	NPD6928	Phase 2
0.6947	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.693	Remote Similarity	NPD8335	Approved
0.693	Remote Similarity	NPD8379	Approved
0.693	Remote Similarity	NPD8378	Approved
0.693	Remote Similarity	NPD8296	Approved
0.693	Remote Similarity	NPD8033	Approved
0.693	Remote Similarity	NPD8380	Approved
0.687	Remote Similarity	NPD6370	Approved
0.6869	Remote Similarity	NPD7637	Suspended
0.6864	Remote Similarity	NPD7736	Approved
0.6842	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6882	Approved
0.678	Remote Similarity	NPD8293	Discontinued
0.6752	Remote Similarity	NPD7492	Approved
0.6737	Remote Similarity	NPD6695	Phase 3
0.6733	Remote Similarity	NPD7748	Approved
0.6726	Remote Similarity	NPD6009	Approved
0.67	Remote Similarity	NPD7515	Phase 2
0.6699	Remote Similarity	NPD7902	Approved
0.6696	Remote Similarity	NPD6054	Approved
0.6695	Remote Similarity	NPD6616	Approved
0.6695	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD7645	Phase 2
0.6667	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD6067	Discontinued
0.6639	Remote Similarity	NPD7078	Approved
0.6635	Remote Similarity	NPD4225	Approved
0.6634	Remote Similarity	NPD8171	Discontinued
0.6606	Remote Similarity	NPD6899	Approved
0.6606	Remote Similarity	NPD6881	Approved
0.6606	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7632	Discontinued
0.6593	Remote Similarity	NPD7339	Approved
0.6593	Remote Similarity	NPD6942	Approved
0.6579	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5739	Approved
0.6574	Remote Similarity	NPD7128	Approved
0.6574	Remote Similarity	NPD6675	Approved
0.6574	Remote Similarity	NPD6402	Approved
0.6559	Remote Similarity	NPD6697	Approved
0.6559	Remote Similarity	NPD6115	Approved
0.6559	Remote Similarity	NPD6118	Approved
0.6559	Remote Similarity	NPD6114	Approved
0.6552	Remote Similarity	NPD6059	Approved
0.6535	Remote Similarity	NPD6411	Approved
0.6529	Remote Similarity	NPD7319	Approved
0.6522	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5697	Approved
0.6496	Remote Similarity	NPD6016	Approved
0.6496	Remote Similarity	NPD6015	Approved
0.6495	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4786	Approved
0.6489	Remote Similarity	NPD6929	Approved
0.6486	Remote Similarity	NPD7102	Approved
0.6486	Remote Similarity	NPD7290	Approved
0.6486	Remote Similarity	NPD6883	Approved
0.6484	Remote Similarity	NPD6924	Approved
0.6484	Remote Similarity	NPD6926	Approved
0.6471	Remote Similarity	NPD5778	Approved
0.6471	Remote Similarity	NPD5779	Approved
0.6465	Remote Similarity	NPD7524	Approved
0.6465	Remote Similarity	NPD7750	Discontinued
0.646	Remote Similarity	NPD4632	Approved
0.6458	Remote Similarity	NPD3667	Approved
0.6455	Remote Similarity	NPD7320	Approved
0.6455	Remote Similarity	NPD6011	Approved
0.6452	Remote Similarity	NPD6932	Approved
0.6452	Remote Similarity	NPD6116	Phase 1
0.6444	Remote Similarity	NPD7150	Approved
0.6444	Remote Similarity	NPD7152	Approved
0.6444	Remote Similarity	NPD7151	Approved
0.6441	Remote Similarity	NPD5988	Approved
0.6429	Remote Similarity	NPD8130	Phase 1
0.6429	Remote Similarity	NPD6617	Approved
0.6429	Remote Similarity	NPD6650	Approved
0.6429	Remote Similarity	NPD6649	Approved
0.6429	Remote Similarity	NPD6869	Approved
0.6429	Remote Similarity	NPD6847	Approved
0.6422	Remote Similarity	NPD6008	Approved
0.6421	Remote Similarity	NPD6931	Approved
0.6421	Remote Similarity	NPD7509	Discontinued
0.6421	Remote Similarity	NPD6930	Phase 2
0.6408	Remote Similarity	NPD7900	Approved
0.6408	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6373	Approved
0.6396	Remote Similarity	NPD6012	Approved
0.6396	Remote Similarity	NPD6372	Approved
0.6396	Remote Similarity	NPD6013	Approved
0.6396	Remote Similarity	NPD6014	Approved
0.6392	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD3669	Approved
0.6383	Remote Similarity	NPD7145	Approved
0.6381	Remote Similarity	NPD6083	Phase 2
0.6381	Remote Similarity	NPD6084	Phase 2
0.6373	Remote Similarity	NPD6079	Approved
0.6372	Remote Similarity	NPD8297	Approved
0.6364	Remote Similarity	NPD3618	Phase 1
0.6364	Remote Similarity	NPD6409	Approved
0.6364	Remote Similarity	NPD5330	Approved
0.6364	Remote Similarity	NPD7521	Approved
0.6364	Remote Similarity	NPD5701	Approved
0.6364	Remote Similarity	NPD6684	Approved
0.6364	Remote Similarity	NPD7334	Approved
0.6364	Remote Similarity	NPD7146	Approved
0.6356	Remote Similarity	NPD8515	Approved
0.6356	Remote Similarity	NPD8513	Phase 3
0.6356	Remote Similarity	NPD8517	Approved
0.6356	Remote Similarity	NPD8516	Approved
0.6355	Remote Similarity	NPD5344	Discontinued
0.6344	Remote Similarity	NPD6933	Approved
0.6344	Remote Similarity	NPD6117	Approved
0.6337	Remote Similarity	NPD6101	Approved
0.6337	Remote Similarity	NPD6051	Approved
0.6337	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5328	Approved
0.6333	Remote Similarity	NPD7143	Approved
0.6333	Remote Similarity	NPD7144	Approved
0.633	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD1811	Approved
0.6304	Remote Similarity	NPD1810	Approved
0.6304	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5776	Phase 2
0.6277	Remote Similarity	NPD6925	Approved
0.6271	Remote Similarity	NPD6319	Approved
0.6262	Remote Similarity	NPD6648	Approved
0.625	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7332	Phase 2
0.625	Remote Similarity	NPD7604	Phase 2
0.625	Remote Similarity	NPD7514	Phase 3
0.6238	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6903	Approved
0.6238	Remote Similarity	NPD6672	Approved
0.6238	Remote Similarity	NPD5737	Approved
0.6237	Remote Similarity	NPD8264	Approved
0.6235	Remote Similarity	NPD1145	Discontinued
0.6222	Remote Similarity	NPD6922	Approved
0.6222	Remote Similarity	NPD6923	Approved
0.6218	Remote Similarity	NPD5983	Phase 2
0.6214	Remote Similarity	NPD7087	Discontinued
0.6186	Remote Similarity	NPD6902	Approved
0.6179	Remote Similarity	NPD6033	Approved
0.6162	Remote Similarity	NPD3133	Approved
0.6162	Remote Similarity	NPD3666	Approved
0.6162	Remote Similarity	NPD3665	Phase 1
0.6154	Remote Similarity	NPD4202	Approved
0.6154	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6336	Discontinued
0.6146	Remote Similarity	NPD6683	Phase 2
0.6139	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4250	Approved
0.6139	Remote Similarity	NPD4251	Approved
0.6132	Remote Similarity	NPD5222	Approved
0.6132	Remote Similarity	NPD5221	Approved
0.6132	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7838	Discovery
0.6111	Remote Similarity	NPD5286	Approved
0.6111	Remote Similarity	NPD4696	Approved
0.6111	Remote Similarity	NPD5285	Approved
0.6102	Remote Similarity	NPD6335	Approved
0.61	Remote Similarity	NPD6893	Approved
0.6075	Remote Similarity	NPD5173	Approved
0.6075	Remote Similarity	NPD4755	Approved
0.6068	Remote Similarity	NPD6868	Approved
0.6061	Remote Similarity	NPD4788	Approved
0.6058	Remote Similarity	NPD5281	Approved
0.6058	Remote Similarity	NPD5284	Approved
0.6055	Remote Similarity	NPD5223	Approved
0.6053	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.605	Remote Similarity	NPD7101	Approved
0.605	Remote Similarity	NPD7100	Approved
0.6042	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4249	Approved
0.6038	Remote Similarity	NPD5695	Phase 3
0.6038	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7991	Discontinued
0.602	Remote Similarity	NPD6898	Phase 1
0.6019	Remote Similarity	NPD5696	Approved
0.6017	Remote Similarity	NPD6317	Approved
0.6017	Remote Similarity	NPD7115	Discovery

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