NPASS Compound

Structure

CID325869 OpenBabel06191716182D 27 28 0 0 1 0 0 0 0 0999 V2000 2.6361 -2.8437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6542 -4.2450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4410 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0886 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -3.6126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9021 -2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0181 -4.0193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -2.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -3.0248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4899 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7406 -3.8382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4899 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0832 1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9021 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 -1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9316 -4.4260 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -2.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6709 2.5316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9497 -5.8273 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4899 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0361 -5.4206 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 7 9 1 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 21 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 20 1 0 0 0 0 16 23 2 0 0 0 0 16 26 1 0 0 0 0 17 26 1 6 0 0 0 18 19 1 0 0 0 0 18 21 1 6 0 0 0 19 22 1 1 0 0 0 20 27 1 0 0 0 0 21 5 1 6 0 0 0 22 6 1 1 0 0 0 22 24 1 0 0 0 0 25 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	380.26
Volume:	407.997
LogP:	3.767
LogD:	3.422
LogS:	-3.355
# Rotatable Bonds:	7
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.303
Synthetic Accessibility Score:	5.415
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.591
MDCK Permeability:	3.64053194061853e-05
Pgp-inhibitor:	0.559
Pgp-substrate:	0.163
Human Intestinal Absorption (HIA):	0.056
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.472
Plasma Protein Binding (PPB):	87.3086929321289%
Volume Distribution (VD):	1.607
Pgp-substrate:	11.44772720336914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.82
CYP2C9-inhibitor:	0.081
CYP2C9-substrate:	0.392
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.363
CYP3A4-inhibitor:	0.425
CYP3A4-substrate:	0.278

ADMET: Excretion

Clearance (CL):	4.541
Half-life (T1/2):	0.197

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.87
Drug-inuced Liver Injury (DILI):	0.486
AMES Toxicity:	0.494
Rat Oral Acute Toxicity:	0.371
Maximum Recommended Daily Dose:	0.754
Skin Sensitization:	0.468
Carcinogencity:	0.289
Eye Corrosion:	0.024
Eye Irritation:	0.06
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: NPC325869

Natural Product ID:	NPC325869
*Common Name:**	Pacificin H
IUPAC Name:	[(1S,2R,5E,7R,9S,10S)-2-(3-hydroperoxy-4-methylpent-4-enyl)-9-hydroxy-2,5,9-trimethyl-7-bicyclo[8.1.0]undec-5-enyl] acetate
Synonyms:	Pacificin H
Standard InCHIKey:	FAXDRDJWQDFFGZ-XVDZUCNCSA-N
Standard InCHI:	InChI=1S/C22H36O5/c1-14(2)20(27-25)8-10-21(5)9-7-15(3)11-17(26-16(4)23)13-22(6,24)19-12-18(19)21/h11,17-20,24-25H,1,7-10,12-13H2,2-6H3/b15-11+/t17-,18-,19-,20?,21+,22-/m0/s1
SMILES:	OOC(C(=C)C)CC[C@@]1(C)CC/C(=C/[C@@H](C[C@]([C@@H]2[C@@H]1C2)(C)O)OC(=O)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479893
PubChem CID:	21574269
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary alcohols

*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
NPO26870	Nephthea pacifica	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[15679321]
NPO26870	Nephthea pacifica	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679321]
NPO26870	Nephthea pacifica	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.01	ug ml-1	PMID[450919]

☑ 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 NPC325869 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	196
0.1-0.2	1556
0.2-0.3	6052
0.3-0.4	16878
0.4-0.5	8381
0.5-0.6	6887
0.6-0.7	2477
0.7-0.8	258
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8354	Intermediate Similarity	NPC474005
0.8293	Intermediate Similarity	NPC231601
0.8289	Intermediate Similarity	NPC472254
0.8267	Intermediate Similarity	NPC101622
0.8158	Intermediate Similarity	NPC4299
0.8148	Intermediate Similarity	NPC474739
0.8101	Intermediate Similarity	NPC476317
0.8072	Intermediate Similarity	NPC49208
0.8072	Intermediate Similarity	NPC23748
0.8049	Intermediate Similarity	NPC474894
0.8046	Intermediate Similarity	NPC469368
0.8025	Intermediate Similarity	NPC471537
0.8	Intermediate Similarity	NPC84360
0.8	Intermediate Similarity	NPC476439
0.7875	Intermediate Similarity	NPC301525
0.7875	Intermediate Similarity	NPC469880
0.7875	Intermediate Similarity	NPC477202
0.7875	Intermediate Similarity	NPC268111
0.7857	Intermediate Similarity	NPC474193
0.7857	Intermediate Similarity	NPC474809
0.7857	Intermediate Similarity	NPC12283
0.7821	Intermediate Similarity	NPC477084
0.7805	Intermediate Similarity	NPC242767
0.7805	Intermediate Similarity	NPC86971
0.7792	Intermediate Similarity	NPC269841
0.7778	Intermediate Similarity	NPC477203
0.7778	Intermediate Similarity	NPC40049
0.7765	Intermediate Similarity	NPC160517
0.7765	Intermediate Similarity	NPC78673
0.7765	Intermediate Similarity	NPC186155
0.775	Intermediate Similarity	NPC113639
0.7722	Intermediate Similarity	NPC477085
0.7701	Intermediate Similarity	NPC45957
0.7701	Intermediate Similarity	NPC166857
0.7701	Intermediate Similarity	NPC471657
0.7692	Intermediate Similarity	NPC469660
0.7647	Intermediate Similarity	NPC311070
0.7647	Intermediate Similarity	NPC472473
0.7619	Intermediate Similarity	NPC229584
0.7619	Intermediate Similarity	NPC112868
0.7619	Intermediate Similarity	NPC14203
0.7619	Intermediate Similarity	NPC475944
0.7595	Intermediate Similarity	NPC477086
0.7595	Intermediate Similarity	NPC477087
0.759	Intermediate Similarity	NPC89128
0.7586	Intermediate Similarity	NPC131813
0.7586	Intermediate Similarity	NPC61527
0.7586	Intermediate Similarity	NPC137253
0.7532	Intermediate Similarity	NPC472266
0.7531	Intermediate Similarity	NPC199445
0.7531	Intermediate Similarity	NPC93213
0.7531	Intermediate Similarity	NPC329852
0.75	Intermediate Similarity	NPC233332
0.75	Intermediate Similarity	NPC476600
0.75	Intermediate Similarity	NPC474765
0.75	Intermediate Similarity	NPC472470
0.75	Intermediate Similarity	NPC131329
0.75	Intermediate Similarity	NPC329763
0.75	Intermediate Similarity	NPC469802
0.7471	Intermediate Similarity	NPC255307
0.7471	Intermediate Similarity	NPC261380
0.7471	Intermediate Similarity	NPC11804
0.747	Intermediate Similarity	NPC474816
0.747	Intermediate Similarity	NPC209135
0.7444	Intermediate Similarity	NPC78973
0.7444	Intermediate Similarity	NPC209816
0.7442	Intermediate Similarity	NPC475989
0.7442	Intermediate Similarity	NPC472377
0.7442	Intermediate Similarity	NPC476927
0.7439	Intermediate Similarity	NPC271070
0.7419	Intermediate Similarity	NPC162346
0.7416	Intermediate Similarity	NPC472810
0.7416	Intermediate Similarity	NPC93411
0.7416	Intermediate Similarity	NPC472809
0.7416	Intermediate Similarity	NPC260343
0.7416	Intermediate Similarity	NPC472378
0.7412	Intermediate Similarity	NPC472471
0.7412	Intermediate Similarity	NPC170303
0.7412	Intermediate Similarity	NPC475481
0.7412	Intermediate Similarity	NPC79277
0.7412	Intermediate Similarity	NPC52861
0.7407	Intermediate Similarity	NPC474758
0.7407	Intermediate Similarity	NPC474551
0.7407	Intermediate Similarity	NPC477204
0.7407	Intermediate Similarity	NPC471525
0.7391	Intermediate Similarity	NPC161998
0.7386	Intermediate Similarity	NPC475461
0.7386	Intermediate Similarity	NPC474045
0.7386	Intermediate Similarity	NPC476104
0.7386	Intermediate Similarity	NPC261253
0.7386	Intermediate Similarity	NPC305475
0.7381	Intermediate Similarity	NPC139712
0.7381	Intermediate Similarity	NPC477088
0.7381	Intermediate Similarity	NPC82488
0.7381	Intermediate Similarity	NPC308545
0.7363	Intermediate Similarity	NPC249034
0.7363	Intermediate Similarity	NPC475972
0.7356	Intermediate Similarity	NPC471302
0.7356	Intermediate Similarity	NPC82297
0.7356	Intermediate Similarity	NPC102048
0.7356	Intermediate Similarity	NPC114979
0.7356	Intermediate Similarity	NPC476804
0.7356	Intermediate Similarity	NPC306951
0.7356	Intermediate Similarity	NPC471301
0.7356	Intermediate Similarity	NPC474776
0.7356	Intermediate Similarity	NPC191476
0.7349	Intermediate Similarity	NPC283619
0.7349	Intermediate Similarity	NPC262747
0.7342	Intermediate Similarity	NPC239373
0.7342	Intermediate Similarity	NPC329989
0.7342	Intermediate Similarity	NPC329656
0.7342	Intermediate Similarity	NPC22301
0.7333	Intermediate Similarity	NPC470734
0.7333	Intermediate Similarity	NPC469866
0.7333	Intermediate Similarity	NPC261320
0.7333	Intermediate Similarity	NPC20946
0.7333	Intermediate Similarity	NPC471342
0.7326	Intermediate Similarity	NPC85772
0.7326	Intermediate Similarity	NPC471298
0.7326	Intermediate Similarity	NPC89555
0.7326	Intermediate Similarity	NPC35556
0.7326	Intermediate Similarity	NPC256112
0.7312	Intermediate Similarity	NPC276110
0.7308	Intermediate Similarity	NPC193029
0.7308	Intermediate Similarity	NPC473357
0.7303	Intermediate Similarity	NPC199382
0.7284	Intermediate Similarity	NPC222244
0.7284	Intermediate Similarity	NPC16349
0.7284	Intermediate Similarity	NPC238425
0.7284	Intermediate Similarity	NPC474543
0.7284	Intermediate Similarity	NPC472018
0.7283	Intermediate Similarity	NPC475838
0.7283	Intermediate Similarity	NPC7349
0.7283	Intermediate Similarity	NPC228451
0.7283	Intermediate Similarity	NPC125674
0.7273	Intermediate Similarity	NPC61503
0.7273	Intermediate Similarity	NPC30984
0.7273	Intermediate Similarity	NPC471344
0.7273	Intermediate Similarity	NPC471795
0.7273	Intermediate Similarity	NPC474369
0.7273	Intermediate Similarity	NPC35933
0.7262	Intermediate Similarity	NPC477089
0.7262	Intermediate Similarity	NPC121200
0.7253	Intermediate Similarity	NPC220216
0.7253	Intermediate Similarity	NPC473448
0.725	Intermediate Similarity	NPC473361
0.725	Intermediate Similarity	NPC329904
0.7241	Intermediate Similarity	NPC475842
0.7241	Intermediate Similarity	NPC471297
0.7241	Intermediate Similarity	NPC473390
0.7241	Intermediate Similarity	NPC161045
0.7241	Intermediate Similarity	NPC131669
0.7241	Intermediate Similarity	NPC42476
0.7241	Intermediate Similarity	NPC474703
0.7237	Intermediate Similarity	NPC217940
0.7234	Intermediate Similarity	NPC57664
0.7229	Intermediate Similarity	NPC170148
0.7222	Intermediate Similarity	NPC24816
0.7216	Intermediate Similarity	NPC183571
0.7215	Intermediate Similarity	NPC272961
0.7215	Intermediate Similarity	NPC276290
0.7209	Intermediate Similarity	NPC172309
0.7209	Intermediate Similarity	NPC117960
0.7209	Intermediate Similarity	NPC327002
0.7209	Intermediate Similarity	NPC40228
0.7209	Intermediate Similarity	NPC315731
0.7209	Intermediate Similarity	NPC184208
0.7209	Intermediate Similarity	NPC141810
0.7209	Intermediate Similarity	NPC25554
0.7209	Intermediate Similarity	NPC14044
0.7209	Intermediate Similarity	NPC325031
0.7209	Intermediate Similarity	NPC8538
0.7209	Intermediate Similarity	NPC471661
0.7204	Intermediate Similarity	NPC472467
0.7204	Intermediate Similarity	NPC105490
0.7204	Intermediate Similarity	NPC474247
0.7204	Intermediate Similarity	NPC298973
0.7204	Intermediate Similarity	NPC104925
0.7204	Intermediate Similarity	NPC469697
0.7195	Intermediate Similarity	NPC71152
0.7195	Intermediate Similarity	NPC190859
0.7191	Intermediate Similarity	NPC476982
0.7191	Intermediate Similarity	NPC50637
0.7191	Intermediate Similarity	NPC329692
0.7191	Intermediate Similarity	NPC471219
0.7191	Intermediate Similarity	NPC311163
0.7191	Intermediate Similarity	NPC477668
0.7191	Intermediate Similarity	NPC150755
0.7191	Intermediate Similarity	NPC116575
0.7188	Intermediate Similarity	NPC130792
0.7176	Intermediate Similarity	NPC233295
0.7176	Intermediate Similarity	NPC476701
0.7176	Intermediate Similarity	NPC100906
0.7174	Intermediate Similarity	NPC329842
0.7174	Intermediate Similarity	NPC177641
0.7174	Intermediate Similarity	NPC72845
0.7174	Intermediate Similarity	NPC124374
0.7174	Intermediate Similarity	NPC234335
0.7172	Intermediate Similarity	NPC9303
0.7172	Intermediate Similarity	NPC16313

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 NPC325869 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	2140
0.2-0.3	3877
0.3-0.4	2144
0.4-0.5	543
0.5-0.6	228
0.6-0.7	35
0.7-0.8	2
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
0.75	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7838	Discovery
0.6966	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6051	Approved
0.6932	Remote Similarity	NPD5209	Approved
0.6897	Remote Similarity	NPD4820	Approved
0.6897	Remote Similarity	NPD4821	Approved
0.6897	Remote Similarity	NPD4819	Approved
0.6897	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4822	Approved
0.6882	Remote Similarity	NPD46	Approved
0.6882	Remote Similarity	NPD6698	Approved
0.686	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7154	Phase 3
0.6768	Remote Similarity	NPD5344	Discontinued
0.6742	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4225	Approved
0.6735	Remote Similarity	NPD7638	Approved
0.6731	Remote Similarity	NPD6371	Approved
0.6709	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD8039	Approved
0.6702	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6667	Remote Similarity	NPD4268	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD5362	Discontinued
0.6632	Remote Similarity	NPD7637	Suspended
0.6632	Remote Similarity	NPD6411	Approved
0.6598	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5779	Approved
0.6562	Remote Similarity	NPD5778	Approved
0.6556	Remote Similarity	NPD6435	Approved
0.6522	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5332	Approved
0.6484	Remote Similarity	NPD5331	Approved
0.6444	Remote Similarity	NPD5369	Approved
0.6444	Remote Similarity	NPD4790	Discontinued
0.6421	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6101	Approved
0.6395	Remote Similarity	NPD6926	Approved
0.6395	Remote Similarity	NPD6924	Approved
0.6392	Remote Similarity	NPD6399	Phase 3
0.6383	Remote Similarity	NPD4250	Approved
0.6383	Remote Similarity	NPD7524	Approved
0.6383	Remote Similarity	NPD4251	Approved
0.6383	Remote Similarity	NPD7750	Discontinued
0.6381	Remote Similarity	NPD6686	Approved
0.6374	Remote Similarity	NPD4269	Approved
0.6374	Remote Similarity	NPD4270	Approved
0.6344	Remote Similarity	NPD1694	Approved
0.6333	Remote Similarity	NPD5368	Approved
0.6333	Remote Similarity	NPD6931	Approved
0.6333	Remote Similarity	NPD6930	Phase 2
0.6327	Remote Similarity	NPD7748	Approved
0.63	Remote Similarity	NPD6083	Phase 2
0.63	Remote Similarity	NPD6084	Phase 2
0.6289	Remote Similarity	NPD7983	Approved
0.6286	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5786	Approved
0.6277	Remote Similarity	NPD4249	Approved
0.6264	Remote Similarity	NPD6902	Approved
0.6263	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD1695	Approved
0.625	Remote Similarity	NPD368	Approved
0.625	Remote Similarity	NPD6933	Approved
0.6238	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6929	Approved
0.6222	Remote Similarity	NPD7645	Phase 2
0.6216	Remote Similarity	NPD7115	Discovery
0.617	Remote Similarity	NPD5363	Approved
0.6154	Remote Similarity	NPD7332	Phase 2
0.6154	Remote Similarity	NPD7525	Registered
0.6154	Remote Similarity	NPD4252	Approved
0.6154	Remote Similarity	NPD7514	Phase 3
0.6139	Remote Similarity	NPD7902	Approved
0.6136	Remote Similarity	NPD8264	Approved
0.6122	Remote Similarity	NPD7087	Discontinued
0.6122	Remote Similarity	NPD7515	Phase 2
0.6111	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD7146	Approved
0.6105	Remote Similarity	NPD7521	Approved
0.6105	Remote Similarity	NPD6409	Approved
0.6105	Remote Similarity	NPD7334	Approved
0.6105	Remote Similarity	NPD5330	Approved
0.6105	Remote Similarity	NPD6684	Approved
0.6078	Remote Similarity	NPD5696	Approved
0.6058	Remote Similarity	NPD7632	Discontinued
0.604	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.604	Remote Similarity	NPD7839	Suspended
0.6038	Remote Similarity	NPD6402	Approved
0.6038	Remote Similarity	NPD7128	Approved
0.6038	Remote Similarity	NPD5739	Approved
0.6038	Remote Similarity	NPD6675	Approved
0.6019	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD7328	Approved
0.6018	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD6893	Approved
0.6	Remote Similarity	NPD6932	Approved
0.6	Remote Similarity	NPD5776	Phase 2
0.6	Remote Similarity	NPD6925	Approved
0.6	Remote Similarity	NPD6053	Discontinued
0.6	Remote Similarity	NPD5282	Discontinued
0.6	Remote Similarity	NPD6927	Phase 3
0.5979	Remote Similarity	NPD6903	Approved
0.5979	Remote Similarity	NPD6672	Approved
0.5979	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD5737	Approved
0.5978	Remote Similarity	NPD7509	Discontinued
0.5965	Remote Similarity	NPD7516	Approved
0.5963	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5693	Phase 1
0.5955	Remote Similarity	NPD7339	Approved
0.5955	Remote Similarity	NPD6942	Approved
0.5941	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD7145	Approved
0.593	Remote Similarity	NPD6922	Approved
0.593	Remote Similarity	NPD6923	Approved
0.5926	Remote Similarity	NPD6881	Approved
0.5926	Remote Similarity	NPD7320	Approved
0.5926	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6899	Approved
0.5914	Remote Similarity	NPD6898	Phase 1
0.5913	Remote Similarity	NPD8377	Approved
0.5913	Remote Similarity	NPD8294	Approved
0.5909	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD342	Phase 1
0.5895	Remote Similarity	NPD4786	Approved
0.5889	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6372	Approved
0.5872	Remote Similarity	NPD6373	Approved
0.587	Remote Similarity	NPD6683	Phase 2
0.5862	Remote Similarity	NPD8033	Approved
0.5862	Remote Similarity	NPD7143	Approved
0.5862	Remote Similarity	NPD8296	Approved
0.5862	Remote Similarity	NPD8378	Approved
0.5862	Remote Similarity	NPD8335	Approved
0.5862	Remote Similarity	NPD7144	Approved
0.5862	Remote Similarity	NPD7503	Approved
0.5862	Remote Similarity	NPD8380	Approved
0.5862	Remote Similarity	NPD8379	Approved
0.5854	Remote Similarity	NPD4194	Approved
0.5854	Remote Similarity	NPD4193	Approved
0.5854	Remote Similarity	NPD4192	Approved
0.5854	Remote Similarity	NPD4191	Approved
0.5851	Remote Similarity	NPD3667	Approved
0.5842	Remote Similarity	NPD7900	Approved
0.5842	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5701	Approved
0.5833	Remote Similarity	NPD5697	Approved
0.5818	Remote Similarity	NPD7102	Approved
0.5818	Remote Similarity	NPD7290	Approved
0.5818	Remote Similarity	NPD6883	Approved
0.58	Remote Similarity	NPD8034	Phase 2
0.58	Remote Similarity	NPD8035	Phase 2
0.5795	Remote Similarity	NPD4243	Approved
0.5795	Remote Similarity	NPD7150	Approved
0.5795	Remote Similarity	NPD7152	Approved
0.5795	Remote Similarity	NPD7151	Approved
0.5773	Remote Similarity	NPD6422	Discontinued
0.5773	Remote Similarity	NPD6098	Approved
0.5766	Remote Similarity	NPD6869	Approved
0.5766	Remote Similarity	NPD6847	Approved
0.5766	Remote Similarity	NPD6617	Approved
0.5766	Remote Similarity	NPD6650	Approved
0.5766	Remote Similarity	NPD6649	Approved
0.5766	Remote Similarity	NPD8130	Phase 1
0.5765	Remote Similarity	NPD7331	Phase 2
0.5758	Remote Similarity	NPD6673	Approved
0.5758	Remote Similarity	NPD6080	Approved
0.5758	Remote Similarity	NPD5370	Suspended
0.5758	Remote Similarity	NPD4753	Phase 2
0.5758	Remote Similarity	NPD6904	Approved
0.5743	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.573	Remote Similarity	NPD4732	Discontinued
0.5729	Remote Similarity	NPD3666	Approved
0.5729	Remote Similarity	NPD3665	Phase 1
0.5729	Remote Similarity	NPD3133	Approved
0.5729	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6014	Approved
0.5727	Remote Similarity	NPD6013	Approved
0.5727	Remote Similarity	NPD6012	Approved
0.5727	Remote Similarity	NPD6413	Approved
0.5714	Remote Similarity	NPD3197	Phase 1
0.5714	Remote Similarity	NPD6882	Approved
0.5714	Remote Similarity	NPD8297	Approved
0.5714	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.57	Remote Similarity	NPD3168	Discontinued
0.5699	Remote Similarity	NPD4195	Approved
0.5688	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.567	Remote Similarity	NPD1696	Phase 3
0.567	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD4785	Approved
0.5667	Remote Similarity	NPD4784	Approved
0.5667	Remote Similarity	NPD7507	Approved
0.5647	Remote Similarity	NPD7341	Phase 2

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