NPASS Compound

Structure

NPC53867 OpenBabel07101719522D 26 28 0 0 1 0 0 0 0 0999 V2000 3.2206 2.7982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7031 -2.6397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1108 -1.7115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0308 -5.5362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0308 -1.6742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0308 -2.6397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1946 -1.1914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7870 2.1297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9508 1.6469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7379 -0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7870 -0.6504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1946 1.7051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7379 1.9620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8670 -3.1224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3585 0.2569 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1946 -0.2259 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3585 1.2224 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6206 0.7396 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8670 -4.0880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0308 0.2569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9508 -0.1677 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7031 -4.5707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8670 -0.2259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0308 -4.5707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0308 1.2224 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 13 2 0 0 0 0 2 14 1 0 0 0 0 4 24 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 14 2 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 11 21 1 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 14 19 1 0 0 0 0 15 10 1 1 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 7 1 1 0 0 0 16 20 1 0 0 0 0 17 12 1 6 0 0 0 18 21 1 1 0 0 0 18 26 1 0 0 0 0 19 22 2 0 0 0 0 19 24 1 0 0 0 0 20 23 2 0 0 0 0 20 25 1 0 0 0 0 21 3 1 1 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.21
Volume:	379.508
LogP:	3.689
LogD:	2.988
LogS:	-3.991
# Rotatable Bonds:	5
TPSA:	65.13
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.435
Synthetic Accessibility Score:	5.199
Fsp3:	0.714
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:	-4.568
MDCK Permeability:	3.933300104108639e-05
Pgp-inhibitor:	0.81
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.887

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.634
Plasma Protein Binding (PPB):	41.909767150878906%
Volume Distribution (VD):	1.194
Pgp-substrate:	66.23051452636719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.081
CYP1A2-substrate:	0.782
CYP2C19-inhibitor:	0.09
CYP2C19-substrate:	0.807
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.839
CYP3A4-substrate:	0.415

ADMET: Excretion

Clearance (CL):	12.048
Half-life (T1/2):	0.114

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.315
Drug-inuced Liver Injury (DILI):	0.445
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.169
Maximum Recommended Daily Dose:	0.51
Skin Sensitization:	0.69
Carcinogencity:	0.255
Eye Corrosion:	0.079
Eye Irritation:	0.091
Respiratory Toxicity:	0.706

Download Data

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

Natural Product: NPC53867

Natural Product ID:	NPC53867
*Common Name:**	Acalycixeniolide H
IUPAC Name:	n.a.
Synonyms:	Acalycixeniolide H
Standard InCHIKey:	CHMJTHCMQMJKCL-HDZIJYMBSA-N
Standard InCHI:	InChI=1S/C21H30O5/c1-13-8-9-18-21(3,26-18)11-10-15-16(20(23)25-12-17(13)15)7-5-6-14(2)19(22)24-4/h6,15-18H,1,5,7-12H2,2-4H3/b14-6+/t15-,16+,17+,18+,21+/m1/s1
SMILES:	C=C1CC[C@H]2[C@](C)(CC[C@@H]3[C@H](CC/C=C(C)/C(=O)OC)C(=O)OC[C@@H]13)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517060
PubChem CID:	9975905
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO32884	acalycigorgia inermis	Species	Acanthogorgiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11325246]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	3.9	ug.mL-1	PMID[456415]

☑ 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 NPC53867 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	210
0.1-0.2	1341
0.2-0.3	5402
0.3-0.4	13579
0.4-0.5	11648
0.5-0.6	6659
0.6-0.7	3442
0.7-0.8	388
0.8-0.85	19
0.85-0.9	3
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9367	High Similarity	NPC475936
0.9277	High Similarity	NPC115179
0.9277	High Similarity	NPC106040
0.9103	High Similarity	NPC474341
0.8961	High Similarity	NPC475861
0.8824	High Similarity	NPC212598
0.8795	High Similarity	NPC474547
0.878	High Similarity	NPC475842
0.8571	High Similarity	NPC474369
0.8537	High Similarity	NPC141810
0.8471	Intermediate Similarity	NPC234038
0.8471	Intermediate Similarity	NPC116575
0.8462	Intermediate Similarity	NPC135703
0.8452	Intermediate Similarity	NPC196487
0.8452	Intermediate Similarity	NPC14575
0.8452	Intermediate Similarity	NPC72464
0.8372	Intermediate Similarity	NPC475703
0.8372	Intermediate Similarity	NPC474765
0.837	Intermediate Similarity	NPC475053
0.8333	Intermediate Similarity	NPC272050
0.8333	Intermediate Similarity	NPC170377
0.8315	Intermediate Similarity	NPC476049
0.8313	Intermediate Similarity	NPC79277
0.8313	Intermediate Similarity	NPC475481
0.8293	Intermediate Similarity	NPC617
0.8214	Intermediate Similarity	NPC35556
0.8193	Intermediate Similarity	NPC474510
0.8182	Intermediate Similarity	NPC166919
0.8171	Intermediate Similarity	NPC128276
0.8161	Intermediate Similarity	NPC231889
0.8125	Intermediate Similarity	NPC476355
0.8118	Intermediate Similarity	NPC272814
0.8095	Intermediate Similarity	NPC325031
0.8095	Intermediate Similarity	NPC471325
0.809	Intermediate Similarity	NPC62815
0.8072	Intermediate Similarity	NPC469617
0.8072	Intermediate Similarity	NPC178277
0.8068	Intermediate Similarity	NPC475902
0.8049	Intermediate Similarity	NPC57744
0.8049	Intermediate Similarity	NPC41780
0.8049	Intermediate Similarity	NPC107668
0.8049	Intermediate Similarity	NPC187568
0.8049	Intermediate Similarity	NPC470240
0.8049	Intermediate Similarity	NPC476794
0.8046	Intermediate Similarity	NPC122502
0.8046	Intermediate Similarity	NPC474045
0.8046	Intermediate Similarity	NPC50637
0.8046	Intermediate Similarity	NPC261253
0.8025	Intermediate Similarity	NPC244166
0.8023	Intermediate Similarity	NPC243618
0.8023	Intermediate Similarity	NPC9868
0.8023	Intermediate Similarity	NPC70424
0.8	Intermediate Similarity	NPC173609
0.7976	Intermediate Similarity	NPC233377
0.7927	Intermediate Similarity	NPC123360
0.7927	Intermediate Similarity	NPC235906
0.7907	Intermediate Similarity	NPC193198
0.7907	Intermediate Similarity	NPC474703
0.7907	Intermediate Similarity	NPC475989
0.7901	Intermediate Similarity	NPC474758
0.7901	Intermediate Similarity	NPC140287
0.7889	Intermediate Similarity	NPC475748
0.7889	Intermediate Similarity	NPC312042
0.7882	Intermediate Similarity	NPC301477
0.7882	Intermediate Similarity	NPC25684
0.7882	Intermediate Similarity	NPC42470
0.7882	Intermediate Similarity	NPC281949
0.7875	Intermediate Similarity	NPC163003
0.7841	Intermediate Similarity	NPC107787
0.7841	Intermediate Similarity	NPC220478
0.7841	Intermediate Similarity	NPC284902
0.7841	Intermediate Similarity	NPC469676
0.7831	Intermediate Similarity	NPC65603
0.7826	Intermediate Similarity	NPC473330
0.7826	Intermediate Similarity	NPC38830
0.7826	Intermediate Similarity	NPC476267
0.7826	Intermediate Similarity	NPC473316
0.7826	Intermediate Similarity	NPC140543
0.7816	Intermediate Similarity	NPC149869
0.7816	Intermediate Similarity	NPC474776
0.7816	Intermediate Similarity	NPC82297
0.7802	Intermediate Similarity	NPC219874
0.7802	Intermediate Similarity	NPC20713
0.7791	Intermediate Similarity	NPC474291
0.7791	Intermediate Similarity	NPC200513
0.7791	Intermediate Similarity	NPC85772
0.7791	Intermediate Similarity	NPC145963
0.7778	Intermediate Similarity	NPC151770
0.7778	Intermediate Similarity	NPC83423
0.7765	Intermediate Similarity	NPC47747
0.775	Intermediate Similarity	NPC475310
0.775	Intermediate Similarity	NPC469660
0.7742	Intermediate Similarity	NPC107476
0.7738	Intermediate Similarity	NPC471220
0.7738	Intermediate Similarity	NPC222210
0.7738	Intermediate Similarity	NPC63445
0.7738	Intermediate Similarity	NPC93763
0.7738	Intermediate Similarity	NPC108816
0.7727	Intermediate Similarity	NPC261380
0.7727	Intermediate Similarity	NPC78089
0.7727	Intermediate Similarity	NPC189311
0.7727	Intermediate Similarity	NPC96621
0.7727	Intermediate Similarity	NPC215364
0.7727	Intermediate Similarity	NPC99395
0.7727	Intermediate Similarity	NPC197903
0.7722	Intermediate Similarity	NPC276290
0.7717	Intermediate Similarity	NPC475838
0.7717	Intermediate Similarity	NPC228451
0.7717	Intermediate Similarity	NPC125674
0.7711	Intermediate Similarity	NPC61863
0.7711	Intermediate Similarity	NPC12740
0.7711	Intermediate Similarity	NPC110461
0.7711	Intermediate Similarity	NPC271070
0.7701	Intermediate Similarity	NPC475622
0.7701	Intermediate Similarity	NPC222358
0.7701	Intermediate Similarity	NPC108045
0.7701	Intermediate Similarity	NPC39588
0.7701	Intermediate Similarity	NPC170286
0.7692	Intermediate Similarity	NPC329857
0.7692	Intermediate Similarity	NPC469718
0.7683	Intermediate Similarity	NPC259599
0.7683	Intermediate Similarity	NPC15499
0.7683	Intermediate Similarity	NPC117746
0.7683	Intermediate Similarity	NPC294434
0.7674	Intermediate Similarity	NPC286229
0.7667	Intermediate Similarity	NPC471047
0.7667	Intermediate Similarity	NPC475906
0.7667	Intermediate Similarity	NPC226863
0.7667	Intermediate Similarity	NPC281516
0.7667	Intermediate Similarity	NPC469653
0.7667	Intermediate Similarity	NPC469631
0.7667	Intermediate Similarity	NPC469628
0.7654	Intermediate Similarity	NPC477084
0.7647	Intermediate Similarity	NPC471740
0.7647	Intermediate Similarity	NPC469620
0.7647	Intermediate Similarity	NPC270126
0.7647	Intermediate Similarity	NPC182550
0.7647	Intermediate Similarity	NPC469690
0.764	Intermediate Similarity	NPC475461
0.764	Intermediate Similarity	NPC279859
0.764	Intermediate Similarity	NPC198314
0.764	Intermediate Similarity	NPC305475
0.764	Intermediate Similarity	NPC38576
0.764	Intermediate Similarity	NPC261721
0.7634	Intermediate Similarity	NPC474247
0.7634	Intermediate Similarity	NPC474035
0.7634	Intermediate Similarity	NPC81386
0.7625	Intermediate Similarity	NPC265574
0.7625	Intermediate Similarity	NPC261398
0.7619	Intermediate Similarity	NPC97516
0.7619	Intermediate Similarity	NPC141789
0.7619	Intermediate Similarity	NPC171204
0.7619	Intermediate Similarity	NPC476028
0.7614	Intermediate Similarity	NPC115786
0.7614	Intermediate Similarity	NPC159635
0.7614	Intermediate Similarity	NPC30486
0.7614	Intermediate Similarity	NPC474359
0.7609	Intermediate Similarity	NPC470379
0.7609	Intermediate Similarity	NPC111114
0.7609	Intermediate Similarity	NPC470373
0.7609	Intermediate Similarity	NPC261607
0.7609	Intermediate Similarity	NPC303697
0.7609	Intermediate Similarity	NPC300312
0.7609	Intermediate Similarity	NPC221282
0.7604	Intermediate Similarity	NPC469551
0.759	Intermediate Similarity	NPC193351
0.759	Intermediate Similarity	NPC226669
0.759	Intermediate Similarity	NPC138408
0.759	Intermediate Similarity	NPC329852
0.759	Intermediate Similarity	NPC155587
0.7586	Intermediate Similarity	NPC471326
0.7586	Intermediate Similarity	NPC221231
0.7582	Intermediate Similarity	NPC284561
0.7582	Intermediate Similarity	NPC295312
0.7561	Intermediate Similarity	NPC58956
0.7561	Intermediate Similarity	NPC295633
0.7561	Intermediate Similarity	NPC269206
0.7558	Intermediate Similarity	NPC223904
0.7558	Intermediate Similarity	NPC281132
0.7558	Intermediate Similarity	NPC302426
0.7558	Intermediate Similarity	NPC304795
0.7558	Intermediate Similarity	NPC69271
0.7558	Intermediate Similarity	NPC276356
0.7558	Intermediate Similarity	NPC103634
0.7558	Intermediate Similarity	NPC74673
0.7556	Intermediate Similarity	NPC478144
0.7556	Intermediate Similarity	NPC312561
0.7556	Intermediate Similarity	NPC160138
0.7556	Intermediate Similarity	NPC72513
0.7556	Intermediate Similarity	NPC478145
0.7553	Intermediate Similarity	NPC474947
0.7553	Intermediate Similarity	NPC14961
0.7553	Intermediate Similarity	NPC270013
0.7553	Intermediate Similarity	NPC33473
0.7553	Intermediate Similarity	NPC470978
0.7553	Intermediate Similarity	NPC470974
0.7532	Intermediate Similarity	NPC217940
0.7529	Intermediate Similarity	NPC267231
0.7529	Intermediate Similarity	NPC472960
0.7529	Intermediate Similarity	NPC299235

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 NPC53867 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	1699
0.2-0.3	3909
0.3-0.4	2255
0.4-0.5	753
0.5-0.6	280
0.6-0.7	56
0.7-0.8	5
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
0.7792	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6698	Approved
0.7692	Intermediate Similarity	NPD46	Approved
0.7528	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1695	Approved
0.7333	Intermediate Similarity	NPD1694	Approved
0.7191	Intermediate Similarity	NPD5209	Approved
0.701	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8039	Approved
0.6947	Remote Similarity	NPD7838	Discovery
0.6947	Remote Similarity	NPD5785	Approved
0.6842	Remote Similarity	NPD6101	Approved
0.6842	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3573	Approved
0.6804	Remote Similarity	NPD5778	Approved
0.6804	Remote Similarity	NPD5779	Approved
0.6774	Remote Similarity	NPD5363	Approved
0.6739	Remote Similarity	NPD7154	Phase 3
0.6739	Remote Similarity	NPD5362	Discontinued
0.6733	Remote Similarity	NPD6648	Approved
0.6702	Remote Similarity	NPD6684	Approved
0.6702	Remote Similarity	NPD7521	Approved
0.6702	Remote Similarity	NPD7334	Approved
0.6702	Remote Similarity	NPD6409	Approved
0.6702	Remote Similarity	NPD7146	Approved
0.6702	Remote Similarity	NPD5330	Approved
0.6701	Remote Similarity	NPD6411	Approved
0.6701	Remote Similarity	NPD5693	Phase 1
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5344	Discontinued
0.6636	Remote Similarity	NPD6371	Approved
0.6634	Remote Similarity	NPD4225	Approved
0.6634	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6686	Approved
0.6577	Remote Similarity	NPD7115	Discovery
0.6571	Remote Similarity	NPD6008	Approved
0.6562	Remote Similarity	NPD6672	Approved
0.6562	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6903	Approved
0.6562	Remote Similarity	NPD5737	Approved
0.6526	Remote Similarity	NPD6422	Discontinued
0.6526	Remote Similarity	NPD5786	Approved
0.6522	Remote Similarity	NPD5369	Approved
0.6514	Remote Similarity	NPD6053	Discontinued
0.6471	Remote Similarity	NPD7638	Approved
0.6452	Remote Similarity	NPD6435	Approved
0.6452	Remote Similarity	NPD4269	Approved
0.6452	Remote Similarity	NPD4270	Approved
0.6444	Remote Similarity	NPD4756	Discovery
0.6436	Remote Similarity	NPD7839	Suspended
0.6429	Remote Similarity	NPD7331	Phase 2
0.6421	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4821	Approved
0.6413	Remote Similarity	NPD4820	Approved
0.6413	Remote Similarity	NPD4822	Approved
0.6413	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4819	Approved
0.6408	Remote Similarity	NPD7640	Approved
0.6408	Remote Similarity	NPD7639	Approved
0.64	Remote Similarity	NPD7900	Approved
0.64	Remote Similarity	NPD5282	Discontinued
0.64	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7748	Approved
0.6374	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7983	Approved
0.6355	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5695	Phase 3
0.6337	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6051	Approved
0.6327	Remote Similarity	NPD6673	Approved
0.6327	Remote Similarity	NPD6904	Approved
0.6327	Remote Similarity	NPD6080	Approved
0.631	Remote Similarity	NPD7341	Phase 2
0.63	Remote Similarity	NPD6399	Phase 3
0.6263	Remote Similarity	NPD5692	Phase 3
0.6239	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD5368	Approved
0.6237	Remote Similarity	NPD4252	Approved
0.6237	Remote Similarity	NPD4695	Discontinued
0.6224	Remote Similarity	NPD5208	Approved
0.6214	Remote Similarity	NPD6083	Phase 2
0.6214	Remote Similarity	NPD6084	Phase 2
0.6214	Remote Similarity	NPD7902	Approved
0.6211	Remote Similarity	NPD5332	Approved
0.6211	Remote Similarity	NPD5331	Approved
0.6204	Remote Similarity	NPD5697	Approved
0.62	Remote Similarity	NPD6050	Approved
0.62	Remote Similarity	NPD5694	Approved
0.62	Remote Similarity	NPD7515	Phase 2
0.6196	Remote Similarity	NPD4268	Approved
0.6196	Remote Similarity	NPD4271	Approved
0.6182	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4790	Discontinued
0.6154	Remote Similarity	NPD5696	Approved
0.6147	Remote Similarity	NPD6881	Approved
0.6147	Remote Similarity	NPD6899	Approved
0.6147	Remote Similarity	NPD6011	Approved
0.6146	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7128	Approved
0.6111	Remote Similarity	NPD6675	Approved
0.6111	Remote Similarity	NPD5739	Approved
0.6111	Remote Similarity	NPD6402	Approved
0.61	Remote Similarity	NPD5207	Approved
0.6091	Remote Similarity	NPD6012	Approved
0.6091	Remote Similarity	NPD6013	Approved
0.6091	Remote Similarity	NPD6014	Approved
0.6078	Remote Similarity	NPD6001	Approved
0.6055	Remote Similarity	NPD5701	Approved
0.6047	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD7102	Approved
0.6036	Remote Similarity	NPD6883	Approved
0.6036	Remote Similarity	NPD7290	Approved
0.602	Remote Similarity	NPD4249	Approved
0.602	Remote Similarity	NPD6098	Approved
0.6	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7320	Approved
0.5982	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD8130	Phase 1
0.5982	Remote Similarity	NPD6650	Approved
0.5982	Remote Similarity	NPD6617	Approved
0.5982	Remote Similarity	NPD6847	Approved
0.5982	Remote Similarity	NPD6649	Approved
0.5982	Remote Similarity	NPD6869	Approved
0.5979	Remote Similarity	NPD3133	Approved
0.5979	Remote Similarity	NPD3668	Phase 3
0.5979	Remote Similarity	NPD3666	Approved
0.5979	Remote Similarity	NPD3665	Phase 1
0.5966	Remote Similarity	NPD7830	Approved
0.5966	Remote Similarity	NPD7642	Approved
0.5966	Remote Similarity	NPD7829	Approved
0.5962	Remote Similarity	NPD7732	Phase 3
0.596	Remote Similarity	NPD4250	Approved
0.596	Remote Similarity	NPD4251	Approved
0.5946	Remote Similarity	NPD6373	Approved
0.5946	Remote Similarity	NPD6372	Approved
0.5938	Remote Similarity	NPD3667	Approved
0.5929	Remote Similarity	NPD8297	Approved
0.5929	Remote Similarity	NPD6882	Approved
0.5918	Remote Similarity	NPD1696	Phase 3
0.5905	Remote Similarity	NPD5959	Approved
0.5897	Remote Similarity	NPD6927	Phase 3
0.5893	Remote Similarity	NPD2067	Discontinued
0.5882	Remote Similarity	NPD6079	Approved
0.5882	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5284	Approved
0.5882	Remote Similarity	NPD5281	Approved
0.5882	Remote Similarity	NPD7637	Suspended
0.5868	Remote Similarity	NPD7507	Approved
0.5865	Remote Similarity	NPD5654	Approved
0.5859	Remote Similarity	NPD5279	Phase 3
0.5859	Remote Similarity	NPD3618	Phase 1
0.5859	Remote Similarity	NPD4519	Discontinued
0.5859	Remote Similarity	NPD4623	Approved
0.5842	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5328	Approved
0.5842	Remote Similarity	NPD4753	Phase 2
0.5841	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5211	Phase 2
0.5833	Remote Similarity	NPD7632	Discontinued
0.5816	Remote Similarity	NPD4786	Approved
0.581	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5221	Approved
0.581	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5222	Approved
0.5804	Remote Similarity	NPD2182	Approved
0.5798	Remote Similarity	NPD8516	Approved
0.5798	Remote Similarity	NPD8517	Approved
0.5798	Remote Similarity	NPD8515	Approved
0.5798	Remote Similarity	NPD8513	Phase 3
0.5794	Remote Similarity	NPD5286	Approved
0.5794	Remote Similarity	NPD4696	Approved
0.5794	Remote Similarity	NPD5285	Approved
0.578	Remote Similarity	NPD6647	Phase 2
0.5776	Remote Similarity	NPD6274	Approved
0.5773	Remote Similarity	NPD4221	Approved
0.5773	Remote Similarity	NPD4223	Phase 3
0.5773	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.576	Remote Similarity	NPD7260	Phase 2
0.5755	Remote Similarity	NPD4755	Approved
0.5755	Remote Similarity	NPD5173	Approved
0.5741	Remote Similarity	NPD5223	Approved
0.5739	Remote Similarity	NPD4632	Approved
0.5738	Remote Similarity	NPD6637	Approved
0.5738	Remote Similarity	NPD8273	Phase 1
0.5728	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD5909	Discontinued
0.5727	Remote Similarity	NPD5141	Approved
0.5726	Remote Similarity	NPD6317	Approved
0.5726	Remote Similarity	NPD7319	Approved
0.5714	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD5210	Approved
0.5714	Remote Similarity	NPD6110	Phase 1
0.5702	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5690	Phase 2
0.57	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD29	Approved
0.5696	Remote Similarity	NPD28	Approved
0.5688	Remote Similarity	NPD5226	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