NPASS Compound

Structure

NPC103171 OpenBabel07101719122D 26 28 0 0 1 0 0 0 0 0999 V2000 1.5388 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1756 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5963 0.2579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 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 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6453 -0.0511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4373 -1.0292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9021 0.6180 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 2 0 0 0 0 4 14 2 0 0 0 0 5 15 1 0 0 0 0 6 22 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 17 1 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 14 17 1 0 0 0 0 15 23 2 0 0 0 0 15 25 1 0 0 0 0 16 12 1 6 0 0 0 16 20 1 0 0 0 0 17 25 1 6 0 0 0 18 11 1 6 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 19 13 1 1 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 21 26 1 0 0 0 0 22 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.25
Volume:	390.65
LogP:	3.798
LogD:	3.751
LogS:	-4.565
# Rotatable Bonds:	3
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.595
Synthetic Accessibility Score:	5.898
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.587
MDCK Permeability:	2.4873161237337627e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	72.3683853149414%
Volume Distribution (VD):	1.405
Pgp-substrate:	18.644758224487305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.792
CYP2C9-inhibitor:	0.081
CYP2C9-substrate:	0.093
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.339
CYP3A4-substrate:	0.418

ADMET: Excretion

Clearance (CL):	5.209
Half-life (T1/2):	0.213

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.542
Drug-inuced Liver Injury (DILI):	0.898
AMES Toxicity:	0.105
Rat Oral Acute Toxicity:	0.158
Maximum Recommended Daily Dose:	0.037
Skin Sensitization:	0.035
Carcinogencity:	0.152
Eye Corrosion:	0.018
Eye Irritation:	0.045
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC103171

Natural Product ID:	NPC103171
*Common Name:**	Pachycladin C
IUPAC Name:	n.a.
Synonyms:	Pachycladin C
Standard InCHIKey:	CDRWIAOABOJFQY-CZIVXSDSSA-N
Standard InCHI:	InChI=1S/C22H34O4/c1-12(2)16-8-7-13(3)19-18-11-14(4)17(25-15(5)23)9-10-22(6,24)21(26-18)20(16)19/h12,16-21,24H,3-4,7-11H2,1-2,5-6H3/t16-,17+,18-,19-,20-,21-,22-/m1/s1
SMILES:	CC(C)[C@H]1CCC(=C)[C@@H]2[C@H]3CC(=C)[C@H](CC[C@](C)([C@@H]([C@H]12)O3)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1096781
PubChem CID:	46833116
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002916] Eunicellane and asbestinane 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
NPO22114	Cladiella pachyclados	Species	Alcyoniidae	Eukaryota	n.a.	red sea soft coral	n.a.	PMID[20420415]
NPO22114	Cladiella pachyclados	Species	Alcyoniidae	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
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	56000.0	nM	PMID[547795]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	17857143.97	nM	PMID[547795]

☑ 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 NPC103171 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	157
0.1-0.2	1545
0.2-0.3	5517
0.3-0.4	14950
0.4-0.5	8516
0.5-0.6	8402
0.6-0.7	3368
0.7-0.8	210
0.8-0.85	7
0.85-0.9	17
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC264610
0.9359	High Similarity	NPC77003
0.9359	High Similarity	NPC118116
0.9136	High Similarity	NPC471379
0.9136	High Similarity	NPC196911
0.9125	High Similarity	NPC5958
0.9125	High Similarity	NPC239308
0.8941	High Similarity	NPC122057
0.8889	High Similarity	NPC127917
0.8831	High Similarity	NPC36479
0.8795	High Similarity	NPC475684
0.8795	High Similarity	NPC321812
0.8795	High Similarity	NPC322922
0.8718	High Similarity	NPC329626
0.8718	High Similarity	NPC293223
0.869	High Similarity	NPC44538
0.8605	High Similarity	NPC471378
0.8605	High Similarity	NPC312471
0.8588	High Similarity	NPC470260
0.8588	High Similarity	NPC75443
0.8588	High Similarity	NPC92370
0.8588	High Similarity	NPC476723
0.8588	High Similarity	NPC476724
0.8506	High Similarity	NPC312805
0.8488	Intermediate Similarity	NPC291875
0.8488	Intermediate Similarity	NPC161560
0.8452	Intermediate Similarity	NPC476725
0.8372	Intermediate Similarity	NPC309656
0.8295	Intermediate Similarity	NPC8729
0.8295	Intermediate Similarity	NPC208839
0.8295	Intermediate Similarity	NPC91251
0.8072	Intermediate Similarity	NPC76054
0.8022	Intermediate Similarity	NPC476720
0.8	Intermediate Similarity	NPC49208
0.7901	Intermediate Similarity	NPC12696
0.7872	Intermediate Similarity	NPC272223
0.7816	Intermediate Similarity	NPC149725
0.7816	Intermediate Similarity	NPC47958
0.7816	Intermediate Similarity	NPC304509
0.7805	Intermediate Similarity	NPC136424
0.7802	Intermediate Similarity	NPC474835
0.7791	Intermediate Similarity	NPC23748
0.7778	Intermediate Similarity	NPC474323
0.7778	Intermediate Similarity	NPC206614
0.7753	Intermediate Similarity	NPC177629
0.7753	Intermediate Similarity	NPC58219
0.7727	Intermediate Similarity	NPC474762
0.7727	Intermediate Similarity	NPC214315
0.7727	Intermediate Similarity	NPC476015
0.7727	Intermediate Similarity	NPC475019
0.7727	Intermediate Similarity	NPC474949
0.7711	Intermediate Similarity	NPC476719
0.7701	Intermediate Similarity	NPC474780
0.7692	Intermediate Similarity	NPC41838
0.7667	Intermediate Similarity	NPC133450
0.7667	Intermediate Similarity	NPC92974
0.7667	Intermediate Similarity	NPC307411
0.766	Intermediate Similarity	NPC111348
0.766	Intermediate Similarity	NPC473244
0.764	Intermediate Similarity	NPC186148
0.7619	Intermediate Similarity	NPC3852
0.7619	Intermediate Similarity	NPC252483
0.7619	Intermediate Similarity	NPC191345
0.7619	Intermediate Similarity	NPC43463
0.7614	Intermediate Similarity	NPC329749
0.7609	Intermediate Similarity	NPC470187
0.7604	Intermediate Similarity	NPC472554
0.7586	Intermediate Similarity	NPC231601
0.7582	Intermediate Similarity	NPC51004
0.7582	Intermediate Similarity	NPC177668
0.7556	Intermediate Similarity	NPC250687
0.7556	Intermediate Similarity	NPC48824
0.7556	Intermediate Similarity	NPC229407
0.7556	Intermediate Similarity	NPC254572
0.7529	Intermediate Similarity	NPC476701
0.7529	Intermediate Similarity	NPC86971
0.7528	Intermediate Similarity	NPC311163
0.7528	Intermediate Similarity	NPC162071
0.7527	Intermediate Similarity	NPC472416
0.7527	Intermediate Similarity	NPC469491
0.7527	Intermediate Similarity	NPC472360
0.7526	Intermediate Similarity	NPC183571
0.7526	Intermediate Similarity	NPC470972
0.7526	Intermediate Similarity	NPC472552
0.75	Intermediate Similarity	NPC188968
0.75	Intermediate Similarity	NPC471747
0.75	Intermediate Similarity	NPC38855
0.75	Intermediate Similarity	NPC475963
0.75	Intermediate Similarity	NPC30515
0.75	Intermediate Similarity	NPC184463
0.75	Intermediate Similarity	NPC151176
0.75	Intermediate Similarity	NPC165180
0.75	Intermediate Similarity	NPC3464
0.7475	Intermediate Similarity	NPC470263
0.7474	Intermediate Similarity	NPC274793
0.7474	Intermediate Similarity	NPC254121
0.7474	Intermediate Similarity	NPC309503
0.7474	Intermediate Similarity	NPC91197
0.7474	Intermediate Similarity	NPC96597
0.7474	Intermediate Similarity	NPC239547
0.7474	Intermediate Similarity	NPC472998
0.7474	Intermediate Similarity	NPC155319
0.7474	Intermediate Similarity	NPC125551
0.7473	Intermediate Similarity	NPC261320
0.7473	Intermediate Similarity	NPC269267
0.7473	Intermediate Similarity	NPC246028
0.7449	Intermediate Similarity	NPC61442
0.7449	Intermediate Similarity	NPC474165
0.7449	Intermediate Similarity	NPC474775
0.7449	Intermediate Similarity	NPC69171
0.7447	Intermediate Similarity	NPC475900
0.7442	Intermediate Similarity	NPC186594
0.7442	Intermediate Similarity	NPC474739
0.7439	Intermediate Similarity	NPC143576
0.7423	Intermediate Similarity	NPC475617
0.7423	Intermediate Similarity	NPC49532
0.7419	Intermediate Similarity	NPC476300
0.7419	Intermediate Similarity	NPC7349
0.7419	Intermediate Similarity	NPC53555
0.7416	Intermediate Similarity	NPC471494
0.7396	Intermediate Similarity	NPC222303
0.7391	Intermediate Similarity	NPC220216
0.7391	Intermediate Similarity	NPC209816
0.7391	Intermediate Similarity	NPC474761
0.7391	Intermediate Similarity	NPC476004
0.7368	Intermediate Similarity	NPC471765
0.7368	Intermediate Similarity	NPC475304
0.7368	Intermediate Similarity	NPC129569
0.7368	Intermediate Similarity	NPC473964
0.7368	Intermediate Similarity	NPC211810
0.7368	Intermediate Similarity	NPC284194
0.7368	Intermediate Similarity	NPC221801
0.7363	Intermediate Similarity	NPC202672
0.7356	Intermediate Similarity	NPC474894
0.7356	Intermediate Similarity	NPC116320
0.7356	Intermediate Similarity	NPC119922
0.7356	Intermediate Similarity	NPC211049
0.7347	Intermediate Similarity	NPC11956
0.7347	Intermediate Similarity	NPC177701
0.734	Intermediate Similarity	NPC39453
0.734	Intermediate Similarity	NPC274588
0.734	Intermediate Similarity	NPC476722
0.734	Intermediate Similarity	NPC256368
0.734	Intermediate Similarity	NPC3359
0.734	Intermediate Similarity	NPC105490
0.7333	Intermediate Similarity	NPC471219
0.7327	Intermediate Similarity	NPC94377
0.7327	Intermediate Similarity	NPC38948
0.7312	Intermediate Similarity	NPC234335
0.7312	Intermediate Similarity	NPC130840
0.7312	Intermediate Similarity	NPC208886
0.7312	Intermediate Similarity	NPC12172
0.7312	Intermediate Similarity	NPC124374
0.7312	Intermediate Similarity	NPC249034
0.7312	Intermediate Similarity	NPC219516
0.7303	Intermediate Similarity	NPC102048
0.7303	Intermediate Similarity	NPC474776
0.73	Intermediate Similarity	NPC470980
0.7294	Intermediate Similarity	NPC40049
0.7294	Intermediate Similarity	NPC84360
0.7292	Intermediate Similarity	NPC473963
0.7292	Intermediate Similarity	NPC98112
0.7292	Intermediate Similarity	NPC26307
0.7283	Intermediate Similarity	NPC474951
0.7283	Intermediate Similarity	NPC473564
0.7273	Intermediate Similarity	NPC474124
0.7273	Intermediate Similarity	NPC23584
0.7273	Intermediate Similarity	NPC216800
0.7273	Intermediate Similarity	NPC99510
0.7263	Intermediate Similarity	NPC259042
0.7263	Intermediate Similarity	NPC275310
0.7263	Intermediate Similarity	NPC230347
0.7263	Intermediate Similarity	NPC286612
0.7263	Intermediate Similarity	NPC6765
0.7263	Intermediate Similarity	NPC36954
0.7263	Intermediate Similarity	NPC93869
0.7263	Intermediate Similarity	NPC86893
0.7263	Intermediate Similarity	NPC276110
0.7263	Intermediate Similarity	NPC292178
0.7263	Intermediate Similarity	NPC107476
0.7263	Intermediate Similarity	NPC469583
0.7263	Intermediate Similarity	NPC157686
0.7255	Intermediate Similarity	NPC206618
0.7255	Intermediate Similarity	NPC42662
0.7253	Intermediate Similarity	NPC471796
0.7253	Intermediate Similarity	NPC190753
0.7253	Intermediate Similarity	NPC474765
0.7253	Intermediate Similarity	NPC471779
0.7245	Intermediate Similarity	NPC308824
0.7245	Intermediate Similarity	NPC98225
0.7245	Intermediate Similarity	NPC11974
0.7241	Intermediate Similarity	NPC233332
0.7241	Intermediate Similarity	NPC474981
0.7241	Intermediate Similarity	NPC469802
0.7234	Intermediate Similarity	NPC212486
0.7234	Intermediate Similarity	NPC81419
0.7234	Intermediate Similarity	NPC99653
0.7234	Intermediate Similarity	NPC475912
0.7234	Intermediate Similarity	NPC179746
0.7229	Intermediate Similarity	NPC477085

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 NPC103171 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	2094
0.2-0.3	3958
0.3-0.4	2074
0.4-0.5	529
0.5-0.6	305
0.6-0.7	33
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
0.7245	Intermediate Similarity	NPD5344	Discontinued
0.7021	Intermediate Similarity	NPD7838	Discovery
0.7021	Intermediate Similarity	NPD6698	Approved
0.7021	Intermediate Similarity	NPD46	Approved
0.697	Remote Similarity	NPD6648	Approved
0.6869	Remote Similarity	NPD4225	Approved
0.6827	Remote Similarity	NPD6686	Approved
0.6731	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7524	Approved
0.67	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6634	Remote Similarity	NPD7640	Approved
0.6634	Remote Similarity	NPD7639	Approved
0.6559	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6695	Phase 3
0.6449	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7983	Approved
0.6429	Remote Similarity	NPD7327	Approved
0.6429	Remote Similarity	NPD7328	Approved
0.6404	Remote Similarity	NPD8033	Approved
0.6392	Remote Similarity	NPD6051	Approved
0.6389	Remote Similarity	NPD6371	Approved
0.6372	Remote Similarity	NPD7516	Approved
0.6364	Remote Similarity	NPD6399	Phase 3
0.6354	Remote Similarity	NPD4251	Approved
0.6354	Remote Similarity	NPD4250	Approved
0.6337	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8294	Approved
0.6316	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8377	Approved
0.6296	Remote Similarity	NPD1145	Discontinued
0.6273	Remote Similarity	NPD6053	Discontinued
0.6263	Remote Similarity	NPD8034	Phase 2
0.6263	Remote Similarity	NPD8035	Phase 2
0.6263	Remote Similarity	NPD7637	Suspended
0.6261	Remote Similarity	NPD8380	Approved
0.6261	Remote Similarity	NPD8379	Approved
0.6261	Remote Similarity	NPD8335	Approved
0.6261	Remote Similarity	NPD7503	Approved
0.6261	Remote Similarity	NPD8296	Approved
0.6261	Remote Similarity	NPD8378	Approved
0.625	Remote Similarity	NPD4249	Approved
0.6239	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD1695	Approved
0.6222	Remote Similarity	NPD6933	Approved
0.62	Remote Similarity	NPD5778	Approved
0.62	Remote Similarity	NPD5779	Approved
0.619	Remote Similarity	NPD7632	Discontinued
0.6186	Remote Similarity	NPD7750	Discontinued
0.617	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD3168	Discontinued
0.6129	Remote Similarity	NPD4820	Approved
0.6129	Remote Similarity	NPD6930	Phase 2
0.6129	Remote Similarity	NPD6931	Approved
0.6129	Remote Similarity	NPD4819	Approved
0.6129	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4821	Approved
0.6129	Remote Similarity	NPD4822	Approved
0.6111	Remote Similarity	NPD6412	Phase 2
0.6053	Remote Similarity	NPD7115	Discovery
0.605	Remote Similarity	NPD7507	Approved
0.6042	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD6929	Approved
0.6	Remote Similarity	NPD6924	Approved
0.6	Remote Similarity	NPD6926	Approved
0.6	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD8513	Phase 3
0.5983	Remote Similarity	NPD8517	Approved
0.5983	Remote Similarity	NPD8516	Approved
0.5983	Remote Similarity	NPD8515	Approved
0.598	Remote Similarity	NPD5282	Discontinued
0.5979	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD7525	Registered
0.5941	Remote Similarity	NPD7087	Discontinued
0.5938	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5362	Discontinued
0.5938	Remote Similarity	NPD3669	Approved
0.5938	Remote Similarity	NPD7154	Phase 3
0.5929	Remote Similarity	NPD4632	Approved
0.5922	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD4271	Approved
0.5914	Remote Similarity	NPD4268	Approved
0.5902	Remote Similarity	NPD7319	Approved
0.59	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.59	Remote Similarity	NPD6101	Approved
0.5895	Remote Similarity	NPD5369	Approved
0.5888	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6008	Approved
0.5856	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6921	Approved
0.5833	Remote Similarity	NPD6435	Approved
0.5825	Remote Similarity	NPD7748	Approved
0.5816	Remote Similarity	NPD6893	Approved
0.581	Remote Similarity	NPD6083	Phase 2
0.581	Remote Similarity	NPD6084	Phase 2
0.581	Remote Similarity	NPD7902	Approved
0.5806	Remote Similarity	NPD6932	Approved
0.5806	Remote Similarity	NPD5776	Phase 2
0.5806	Remote Similarity	NPD6925	Approved
0.5789	Remote Similarity	NPD7514	Phase 3
0.5789	Remote Similarity	NPD7332	Phase 2
0.5789	Remote Similarity	NPD7509	Discontinued
0.5784	Remote Similarity	NPD6411	Approved
0.5773	Remote Similarity	NPD5332	Approved
0.5773	Remote Similarity	NPD5331	Approved
0.5769	Remote Similarity	NPD5695	Phase 3
0.5763	Remote Similarity	NPD6319	Approved
0.5761	Remote Similarity	NPD6942	Approved
0.5761	Remote Similarity	NPD7339	Approved
0.5758	Remote Similarity	NPD7521	Approved
0.5758	Remote Similarity	NPD5330	Approved
0.5758	Remote Similarity	NPD7334	Approved
0.5758	Remote Similarity	NPD6684	Approved
0.5758	Remote Similarity	NPD7146	Approved
0.5758	Remote Similarity	NPD6409	Approved
0.5745	Remote Similarity	NPD7145	Approved
0.5738	Remote Similarity	NPD8074	Phase 3
0.5729	Remote Similarity	NPD6898	Phase 1
0.5729	Remote Similarity	NPD4790	Discontinued
0.5727	Remote Similarity	NPD6675	Approved
0.5727	Remote Similarity	NPD5739	Approved
0.5727	Remote Similarity	NPD5357	Phase 1
0.5727	Remote Similarity	NPD6640	Phase 3
0.5727	Remote Similarity	NPD7128	Approved
0.5727	Remote Similarity	NPD6402	Approved
0.5714	Remote Similarity	NPD4786	Approved
0.5702	Remote Similarity	NPD7492	Approved
0.5702	Remote Similarity	NPD8297	Approved
0.57	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD371	Approved
0.5686	Remote Similarity	NPD5785	Approved
0.5684	Remote Similarity	NPD6683	Phase 2
0.567	Remote Similarity	NPD3667	Approved
0.567	Remote Similarity	NPD4269	Approved
0.567	Remote Similarity	NPD4270	Approved
0.5657	Remote Similarity	NPD1694	Approved
0.5656	Remote Similarity	NPD6616	Approved
0.5652	Remote Similarity	NPD1810	Approved
0.5652	Remote Similarity	NPD1811	Approved
0.5644	Remote Similarity	NPD5737	Approved
0.5644	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD6903	Approved
0.5644	Remote Similarity	NPD6672	Approved
0.5641	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD6009	Approved
0.5631	Remote Similarity	NPD7515	Phase 2
0.5631	Remote Similarity	NPD5693	Phase 1
0.563	Remote Similarity	NPD6054	Approved
0.563	Remote Similarity	NPD6059	Approved
0.5625	Remote Similarity	NPD6881	Approved
0.5625	Remote Similarity	NPD5368	Approved
0.5625	Remote Similarity	NPD7320	Approved
0.5625	Remote Similarity	NPD6899	Approved
0.562	Remote Similarity	NPD7604	Phase 2
0.5612	Remote Similarity	NPD4788	Approved
0.5612	Remote Similarity	NPD6110	Phase 1
0.561	Remote Similarity	NPD8293	Discontinued
0.561	Remote Similarity	NPD7078	Approved
0.5607	Remote Similarity	NPD5696	Approved
0.56	Remote Similarity	NPD5786	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