NPASS Compound

Structure

NPC471367 OpenBabel07101719522D 33 35 0 0 1 0 0 0 0 0999 V2000 -6.7419 1.0526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7696 2.7365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6949 -0.4057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5149 3.9693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6965 -0.5568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6181 -2.9905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3391 1.8946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7696 1.0526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3113 1.8946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0110 -0.4057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8252 1.0526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1690 0.0804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3271 2.5109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0110 2.5109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2835 1.8946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8530 0.0804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3271 4.4554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9970 0.3678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9676 -2.2680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1690 2.9970 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3271 1.5387 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0110 1.5387 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3954 0.8882 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9669 0.1016 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8530 1.0526 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1690 1.0526 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3271 5.4276 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9479 0.5699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0166 -2.4702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1690 3.9693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3464 1.0903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2680 -1.3434 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 8 2 0 0 0 0 2 15 2 0 0 0 0 3 16 1 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 15 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 25 1 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 14 20 1 0 0 0 0 14 22 1 0 0 0 0 16 25 1 6 0 0 0 17 27 2 0 0 0 0 17 30 1 0 0 0 0 18 28 2 0 0 0 0 18 31 1 0 0 0 0 19 29 2 0 0 0 0 19 32 1 0 0 0 0 20 30 1 1 0 0 0 21 23 1 0 0 0 0 21 26 1 6 0 0 0 22 25 1 1 0 0 0 22 26 1 0 0 0 0 23 31 1 6 0 0 0 23 33 1 0 0 0 0 24 26 1 6 0 0 0 24 32 1 0 0 0 0 24 33 1 0 0 0 0 25 7 1 1 0 0 0 26 12 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.26
Volume:	480.932
LogP:	3.632
LogD:	3.036
LogS:	-4.555
# Rotatable Bonds:	10
TPSA:	88.13
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.308
Synthetic Accessibility Score:	5.585
Fsp3:	0.731
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:	-4.745
MDCK Permeability:	6.341872358461842e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.109

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.227
Plasma Protein Binding (PPB):	68.24755096435547%
Volume Distribution (VD):	2.051
Pgp-substrate:	40.07079315185547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.146
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.416
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	2.924
Half-life (T1/2):	0.38

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.933
Drug-inuced Liver Injury (DILI):	0.926
AMES Toxicity:	0.941
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.799
Skin Sensitization:	0.957
Carcinogencity:	0.428
Eye Corrosion:	0.282
Eye Irritation:	0.177
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC471367

Natural Product ID:	NPC471367
*Common Name:**	Rel-(2R,4S,5R,8S,9S,10R,18S,19R)-2,18,19-Triacetoxycleroda-13(16),14-Dien-18,19-Oxolane
IUPAC Name:	[(1R,3S,3aS,5R,6aR,7S,8S,10aR)-1,3-diacetyloxy-7,8-dimethyl-7-(3-methylidenepent-4-enyl)-1,3,3a,4,5,6,6a,8,9,10-decahydrobenzo[d][2]benzofuran-5-yl] acetate
Synonyms:
Standard InCHIKey:	CCKILWOWDZILRL-VRQSGIKBSA-N
Standard InCHI:	InChI=1S/C26H38O7/c1-8-15(2)9-11-25(7)16(3)10-12-26-21(13-20(14-22(25)26)30-17(4)27)23(31-18(5)28)33-24(26)32-19(6)29/h8,16,20-24H,1-2,9-14H2,3-7H3/t16-,20-,21+,22+,23+,24-,25-,26-/m0/s1
SMILES:	C=CC(=C)CC[C@@]1(C)[C@@H](C)CC[C@]23[C@@H]1C[C@@H](OC(=O)C)C[C@@H]3[C@@H](O[C@@H]2OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419876
PubChem CID:	73346138
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	=	56900.0	nM	PMID[553325]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	66200.0	nM	PMID[553325]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	38200.0	nM	PMID[553325]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	20000.0	nM	PMID[553325]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	36100.0	nM	PMID[553325]

☑ 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 NPC471367 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	182
0.1-0.2	1549
0.2-0.3	6341
0.3-0.4	15243
0.4-0.5	7587
0.5-0.6	6313
0.6-0.7	4914
0.7-0.8	527
0.8-0.85	35
0.85-0.9	0
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC471369
0.9512	High Similarity	NPC263079
0.9506	High Similarity	NPC471368
0.9286	High Similarity	NPC471371
0.9286	High Similarity	NPC471370
0.8652	High Similarity	NPC472189
0.8652	High Similarity	NPC471362
0.8652	High Similarity	NPC471372
0.8636	High Similarity	NPC12297
0.8556	High Similarity	NPC171598
0.8462	Intermediate Similarity	NPC472188
0.837	Intermediate Similarity	NPC318917
0.837	Intermediate Similarity	NPC476800
0.837	Intermediate Similarity	NPC472186
0.837	Intermediate Similarity	NPC471366
0.8352	Intermediate Similarity	NPC8954
0.8352	Intermediate Similarity	NPC94905
0.8333	Intermediate Similarity	NPC88507
0.828	Intermediate Similarity	NPC473204
0.828	Intermediate Similarity	NPC473545
0.828	Intermediate Similarity	NPC472187
0.8261	Intermediate Similarity	NPC198549
0.8261	Intermediate Similarity	NPC113976
0.8222	Intermediate Similarity	NPC163902
0.8152	Intermediate Similarity	NPC311166
0.8105	Intermediate Similarity	NPC238397
0.8105	Intermediate Similarity	NPC471363
0.8095	Intermediate Similarity	NPC473685
0.8065	Intermediate Similarity	NPC471770
0.8065	Intermediate Similarity	NPC98112
0.8065	Intermediate Similarity	NPC278939
0.8065	Intermediate Similarity	NPC473555
0.8043	Intermediate Similarity	NPC230347
0.8043	Intermediate Similarity	NPC286612
0.8043	Intermediate Similarity	NPC275310
0.8041	Intermediate Similarity	NPC218158
0.8021	Intermediate Similarity	NPC134270
0.8021	Intermediate Similarity	NPC7613
0.8021	Intermediate Similarity	NPC475889
0.8021	Intermediate Similarity	NPC7644
0.8021	Intermediate Similarity	NPC127933
0.7979	Intermediate Similarity	NPC157739
0.7978	Intermediate Similarity	NPC144069
0.7938	Intermediate Similarity	NPC81567
0.7938	Intermediate Similarity	NPC473207
0.7938	Intermediate Similarity	NPC264867
0.7938	Intermediate Similarity	NPC470321
0.7938	Intermediate Similarity	NPC201880
0.7935	Intermediate Similarity	NPC128488
0.7935	Intermediate Similarity	NPC211238
0.7935	Intermediate Similarity	NPC304968
0.7895	Intermediate Similarity	NPC161527
0.7895	Intermediate Similarity	NPC317019
0.7895	Intermediate Similarity	NPC20113
0.7895	Intermediate Similarity	NPC477972
0.7895	Intermediate Similarity	NPC219285
0.7895	Intermediate Similarity	NPC477971
0.7895	Intermediate Similarity	NPC228251
0.7895	Intermediate Similarity	NPC477968
0.7889	Intermediate Similarity	NPC293044
0.7882	Intermediate Similarity	NPC475456
0.7882	Intermediate Similarity	NPC471216
0.7882	Intermediate Similarity	NPC469802
0.7882	Intermediate Similarity	NPC269791
0.7882	Intermediate Similarity	NPC471217
0.7872	Intermediate Similarity	NPC97867
0.7857	Intermediate Similarity	NPC252296
0.7857	Intermediate Similarity	NPC172867
0.7841	Intermediate Similarity	NPC164424
0.7835	Intermediate Similarity	NPC120009
0.7826	Intermediate Similarity	NPC474835
0.7816	Intermediate Similarity	NPC473742
0.7812	Intermediate Similarity	NPC119467
0.7812	Intermediate Similarity	NPC475767
0.7791	Intermediate Similarity	NPC71541
0.7778	Intermediate Similarity	NPC184512
0.7778	Intermediate Similarity	NPC125423
0.7778	Intermediate Similarity	NPC88013
0.7778	Intermediate Similarity	NPC109376
0.7755	Intermediate Similarity	NPC31430
0.7755	Intermediate Similarity	NPC85593
0.7742	Intermediate Similarity	NPC477722
0.7732	Intermediate Similarity	NPC154452
0.7732	Intermediate Similarity	NPC470571
0.7727	Intermediate Similarity	NPC299963
0.7727	Intermediate Similarity	NPC102048
0.7717	Intermediate Similarity	NPC120539
0.7717	Intermediate Similarity	NPC474631
0.7708	Intermediate Similarity	NPC324841
0.7708	Intermediate Similarity	NPC146188
0.7701	Intermediate Similarity	NPC472504
0.77	Intermediate Similarity	NPC470024
0.77	Intermediate Similarity	NPC128795
0.77	Intermediate Similarity	NPC217921
0.77	Intermediate Similarity	NPC311223
0.77	Intermediate Similarity	NPC224660
0.77	Intermediate Similarity	NPC135015
0.77	Intermediate Similarity	NPC48548
0.7692	Intermediate Similarity	NPC473058
0.7683	Intermediate Similarity	NPC12680
0.7677	Intermediate Similarity	NPC291414
0.7677	Intermediate Similarity	NPC470055
0.7677	Intermediate Similarity	NPC470056
0.7667	Intermediate Similarity	NPC264546
0.7634	Intermediate Similarity	NPC246860
0.7629	Intermediate Similarity	NPC121072
0.7629	Intermediate Similarity	NPC21064
0.7624	Intermediate Similarity	NPC316974
0.7624	Intermediate Similarity	NPC40728
0.7614	Intermediate Similarity	NPC475820
0.7614	Intermediate Similarity	NPC474346
0.7614	Intermediate Similarity	NPC474284
0.7614	Intermediate Similarity	NPC213737
0.7614	Intermediate Similarity	NPC474253
0.7609	Intermediate Similarity	NPC159876
0.7609	Intermediate Similarity	NPC469403
0.7604	Intermediate Similarity	NPC477928
0.76	Intermediate Similarity	NPC475074
0.7582	Intermediate Similarity	NPC106332
0.7582	Intermediate Similarity	NPC470612
0.7582	Intermediate Similarity	NPC470613
0.7576	Intermediate Similarity	NPC470043
0.7576	Intermediate Similarity	NPC470057
0.7576	Intermediate Similarity	NPC470062
0.7576	Intermediate Similarity	NPC470064
0.7576	Intermediate Similarity	NPC470061
0.7576	Intermediate Similarity	NPC470059
0.7576	Intermediate Similarity	NPC470058
0.7576	Intermediate Similarity	NPC470060
0.7556	Intermediate Similarity	NPC118266
0.7553	Intermediate Similarity	NPC96736
0.7553	Intermediate Similarity	NPC178949
0.7553	Intermediate Similarity	NPC305160
0.7549	Intermediate Similarity	NPC119550
0.7549	Intermediate Similarity	NPC316708
0.7527	Intermediate Similarity	NPC48463
0.75	Intermediate Similarity	NPC2096
0.75	Intermediate Similarity	NPC96597
0.75	Intermediate Similarity	NPC239547
0.75	Intermediate Similarity	NPC91197
0.75	Intermediate Similarity	NPC208912
0.75	Intermediate Similarity	NPC125551
0.75	Intermediate Similarity	NPC309503
0.75	Intermediate Similarity	NPC155319
0.75	Intermediate Similarity	NPC473199
0.75	Intermediate Similarity	NPC470819
0.75	Intermediate Similarity	NPC16265
0.75	Intermediate Similarity	NPC170633
0.7476	Intermediate Similarity	NPC470026
0.7476	Intermediate Similarity	NPC17791
0.7475	Intermediate Similarity	NPC474575
0.7475	Intermediate Similarity	NPC471364
0.7475	Intermediate Similarity	NPC132395
0.7475	Intermediate Similarity	NPC471365
0.7474	Intermediate Similarity	NPC477969
0.7474	Intermediate Similarity	NPC477970
0.7474	Intermediate Similarity	NPC100892
0.7474	Intermediate Similarity	NPC135224
0.7473	Intermediate Similarity	NPC175293
0.7471	Intermediate Similarity	NPC304194
0.7451	Intermediate Similarity	NPC206618
0.7451	Intermediate Similarity	NPC305939
0.7451	Intermediate Similarity	NPC112457
0.7447	Intermediate Similarity	NPC473678
0.7447	Intermediate Similarity	NPC277721
0.7447	Intermediate Similarity	NPC267266
0.7447	Intermediate Similarity	NPC7349
0.7444	Intermediate Similarity	NPC235402
0.7444	Intermediate Similarity	NPC472442
0.7426	Intermediate Similarity	NPC293512
0.7426	Intermediate Similarity	NPC234160
0.7423	Intermediate Similarity	NPC5358
0.7423	Intermediate Similarity	NPC216260
0.7423	Intermediate Similarity	NPC473154
0.7419	Intermediate Similarity	NPC474249
0.7419	Intermediate Similarity	NPC10274
0.7419	Intermediate Similarity	NPC194485
0.7419	Intermediate Similarity	NPC470817
0.7419	Intermediate Similarity	NPC53890
0.7419	Intermediate Similarity	NPC123252
0.7419	Intermediate Similarity	NPC261990
0.7419	Intermediate Similarity	NPC219937
0.7419	Intermediate Similarity	NPC475776
0.7416	Intermediate Similarity	NPC474789
0.7416	Intermediate Similarity	NPC472440
0.7416	Intermediate Similarity	NPC52108
0.7416	Intermediate Similarity	NPC127917
0.7412	Intermediate Similarity	NPC92489
0.7404	Intermediate Similarity	NPC321272
0.7404	Intermediate Similarity	NPC317460
0.7404	Intermediate Similarity	NPC470025
0.7404	Intermediate Similarity	NPC328074
0.74	Intermediate Similarity	NPC244247
0.74	Intermediate Similarity	NPC173583
0.7396	Intermediate Similarity	NPC164750
0.7391	Intermediate Similarity	NPC160304
0.7391	Intermediate Similarity	NPC473879
0.7391	Intermediate Similarity	NPC291665
0.7381	Intermediate Similarity	NPC71152
0.7379	Intermediate Similarity	NPC101450

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 NPC471367 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1837
0.2-0.3	4365
0.3-0.4	1941
0.4-0.5	431
0.5-0.6	252
0.6-0.7	164
0.7-0.8	0
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
0.69	Remote Similarity	NPD7638	Approved
0.6857	Remote Similarity	NPD6686	Approved
0.6852	Remote Similarity	NPD8133	Approved
0.6832	Remote Similarity	NPD7640	Approved
0.6832	Remote Similarity	NPD7639	Approved
0.6804	Remote Similarity	NPD8034	Phase 2
0.6804	Remote Similarity	NPD8035	Phase 2
0.6762	Remote Similarity	NPD6412	Phase 2
0.6757	Remote Similarity	NPD7328	Approved
0.6757	Remote Similarity	NPD7327	Approved
0.6735	Remote Similarity	NPD6399	Phase 3
0.6726	Remote Similarity	NPD7503	Approved
0.6696	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7900	Approved
0.6637	Remote Similarity	NPD8377	Approved
0.6637	Remote Similarity	NPD8294	Approved
0.6636	Remote Similarity	NPD8132	Clinical (unspecified phase)
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
0.6598	Remote Similarity	NPD6051	Approved
0.6579	Remote Similarity	NPD8033	Approved
0.6579	Remote Similarity	NPD8296	Approved
0.6579	Remote Similarity	NPD8380	Approved
0.6579	Remote Similarity	NPD8335	Approved
0.6579	Remote Similarity	NPD8379	Approved
0.6579	Remote Similarity	NPD8378	Approved
0.6543	Remote Similarity	NPD1145	Discontinued
0.6526	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD7736	Approved
0.6522	Remote Similarity	NPD7525	Registered
0.6522	Remote Similarity	NPD6370	Approved
0.6522	Remote Similarity	NPD6928	Phase 2
0.65	Remote Similarity	NPD7748	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)
0.6471	Remote Similarity	NPD7902	Approved
0.6465	Remote Similarity	NPD7637	Suspended
0.6455	Remote Similarity	NPD6882	Approved
0.6441	Remote Similarity	NPD8293	Discontinued
0.6421	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7492	Approved
0.6383	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6009	Approved
0.6356	Remote Similarity	NPD7507	Approved
0.6356	Remote Similarity	NPD6616	Approved
0.6348	Remote Similarity	NPD6054	Approved
0.6325	Remote Similarity	NPD6067	Discontinued
0.6325	Remote Similarity	NPD8328	Phase 3
0.6316	Remote Similarity	NPD6695	Phase 3
0.6303	Remote Similarity	NPD7078	Approved
0.63	Remote Similarity	NPD7515	Phase 2
0.6275	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD2687	Approved
0.625	Remote Similarity	NPD2254	Approved
0.625	Remote Similarity	NPD2686	Approved
0.6239	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6881	Approved
0.6239	Remote Similarity	NPD6899	Approved
0.6238	Remote Similarity	NPD8171	Discontinued
0.6237	Remote Similarity	NPD7645	Phase 2
0.6228	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD7632	Discontinued
0.6224	Remote Similarity	NPD3573	Approved
0.6207	Remote Similarity	NPD6059	Approved
0.6204	Remote Similarity	NPD6675	Approved
0.6204	Remote Similarity	NPD7128	Approved
0.6204	Remote Similarity	NPD5739	Approved
0.6204	Remote Similarity	NPD6402	Approved
0.6198	Remote Similarity	NPD7319	Approved
0.619	Remote Similarity	NPD6648	Approved
0.6186	Remote Similarity	NPD1694	Approved
0.6154	Remote Similarity	NPD6016	Approved
0.6154	Remote Similarity	NPD7339	Approved
0.6154	Remote Similarity	NPD6942	Approved
0.6154	Remote Similarity	NPD6015	Approved
0.6147	Remote Similarity	NPD5697	Approved
0.6146	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD3669	Approved
0.6139	Remote Similarity	NPD6411	Approved
0.6129	Remote Similarity	NPD6697	Approved
0.6129	Remote Similarity	NPD6118	Approved
0.6129	Remote Similarity	NPD6115	Approved
0.6129	Remote Similarity	NPD6114	Approved
0.6126	Remote Similarity	NPD6883	Approved
0.6126	Remote Similarity	NPD7102	Approved
0.6126	Remote Similarity	NPD7290	Approved
0.6122	Remote Similarity	NPD6098	Approved
0.6106	Remote Similarity	NPD4632	Approved
0.6105	Remote Similarity	NPD1779	Approved
0.6105	Remote Similarity	NPD1780	Approved
0.6102	Remote Similarity	NPD5988	Approved
0.61	Remote Similarity	NPD6673	Approved
0.61	Remote Similarity	NPD6904	Approved
0.61	Remote Similarity	NPD6080	Approved
0.6091	Remote Similarity	NPD6011	Approved
0.6091	Remote Similarity	NPD7320	Approved
0.6087	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4786	Approved
0.6082	Remote Similarity	NPD3668	Phase 3
0.6078	Remote Similarity	NPD5779	Approved
0.6078	Remote Similarity	NPD5778	Approved
0.6071	Remote Similarity	NPD6869	Approved
0.6071	Remote Similarity	NPD6617	Approved
0.6071	Remote Similarity	NPD6650	Approved
0.6071	Remote Similarity	NPD6649	Approved
0.6071	Remote Similarity	NPD6847	Approved
0.6071	Remote Similarity	NPD8130	Phase 1
0.6064	Remote Similarity	NPD6929	Approved
0.6061	Remote Similarity	NPD7524	Approved
0.6061	Remote Similarity	NPD7750	Discontinued
0.6044	Remote Similarity	NPD6926	Approved
0.6044	Remote Similarity	NPD6924	Approved
0.6042	Remote Similarity	NPD3667	Approved
0.604	Remote Similarity	NPD5207	Approved
0.6036	Remote Similarity	NPD6012	Approved
0.6036	Remote Similarity	NPD6014	Approved
0.6036	Remote Similarity	NPD6372	Approved
0.6036	Remote Similarity	NPD6013	Approved
0.6036	Remote Similarity	NPD6373	Approved
0.6022	Remote Similarity	NPD6932	Approved
0.6022	Remote Similarity	NPD6116	Phase 1
0.6018	Remote Similarity	NPD8297	Approved
0.6017	Remote Similarity	NPD8517	Approved
0.6017	Remote Similarity	NPD8513	Phase 3
0.6017	Remote Similarity	NPD8515	Approved
0.6017	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD7150	Approved
0.6	Remote Similarity	NPD5777	Approved
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6930	Phase 2
0.6	Remote Similarity	NPD7151	Approved
0.6	Remote Similarity	NPD7509	Discontinued
0.6	Remote Similarity	NPD6931	Approved
0.6	Remote Similarity	NPD7152	Approved
0.5981	Remote Similarity	NPD5344	Discontinued
0.598	Remote Similarity	NPD6050	Approved
0.598	Remote Similarity	NPD5694	Approved
0.598	Remote Similarity	NPD6079	Approved
0.5963	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.596	Remote Similarity	NPD3618	Phase 1
0.5957	Remote Similarity	NPD7145	Approved
0.5943	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6101	Approved
0.5941	Remote Similarity	NPD5328	Approved
0.5941	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6319	Approved
0.5929	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7604	Phase 2
0.5914	Remote Similarity	NPD6933	Approved
0.5914	Remote Similarity	NPD6117	Approved
0.5905	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD7144	Approved
0.5889	Remote Similarity	NPD7143	Approved
0.5882	Remote Similarity	NPD5692	Phase 3
0.5882	Remote Similarity	NPD5983	Phase 2
0.5882	Remote Similarity	NPD3168	Discontinued
0.587	Remote Similarity	NPD1811	Approved
0.587	Remote Similarity	NPD1810	Approved
0.587	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6001	Approved
0.5854	Remote Similarity	NPD6033	Approved
0.5851	Remote Similarity	NPD6925	Approved
0.5851	Remote Similarity	NPD5776	Phase 2
0.5842	Remote Similarity	NPD5208	Approved
0.5841	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7514	Phase 3
0.5833	Remote Similarity	NPD7332	Phase 2
0.5825	Remote Similarity	NPD7087	Discontinued
0.5825	Remote Similarity	NPD5693	Phase 1
0.5825	Remote Similarity	NPD5281	Approved
0.5825	Remote Similarity	NPD5284	Approved
0.582	Remote Similarity	NPD6336	Discontinued
0.581	Remote Similarity	NPD7991	Discontinued
0.581	Remote Similarity	NPD5695	Phase 3
0.5806	Remote Similarity	NPD8264	Approved
0.5806	Remote Similarity	NPD8039	Approved
0.5794	Remote Similarity	NPD5696	Approved
0.5778	Remote Similarity	NPD6923	Approved
0.5778	Remote Similarity	NPD6922	Approved
0.5773	Remote Similarity	NPD6902	Approved
0.5769	Remote Similarity	NPD4202	Approved
0.5763	Remote Similarity	NPD6335	Approved
0.5758	Remote Similarity	NPD3133	Approved
0.5758	Remote Similarity	NPD3665	Phase 1
0.5758	Remote Similarity	NPD3666	Approved
0.5755	Remote Similarity	NPD5222	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