NPASS Compound

Structure

NPC44538 OpenBabel07101719132D 31 33 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 -1.1756 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4049 2.7321 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 2.9049 1.8660 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 3.2709 0.5000 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 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.7321 0.0000 C 0 0 0 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 3.2709 -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 2.4049 -1.0000 0.0000 C 0 0 1 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 2.4049 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 -3.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9049 3.5981 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 4.1369 -1.0000 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 0.5000 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9049 1.8660 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 1 0 0 0 0 5 15 1 0 0 0 0 6 23 1 0 0 0 0 7 24 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 23 1 0 0 0 0 10 13 1 0 0 0 0 11 17 1 0 0 0 0 11 24 1 0 0 0 0 13 16 1 0 0 0 0 14 25 2 0 0 0 0 14 30 1 0 0 0 0 15 26 2 0 0 0 0 15 31 1 0 0 0 0 16 27 1 6 0 0 0 17 19 1 0 0 0 0 17 28 1 1 0 0 0 18 10 1 6 0 0 0 18 21 1 0 0 0 0 18 29 1 0 0 0 0 19 12 1 6 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 24 1 0 0 0 0 22 23 1 0 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.26
Volume:	451.613
LogP:	2.415
LogD:	1.665
LogS:	-2.901
# Rotatable Bonds:	5
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.516
Synthetic Accessibility Score:	6.24
Fsp3:	0.833
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:	-4.857
MDCK Permeability:	8.017965592443943e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.893
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	53.166385650634766%
Volume Distribution (VD):	1.174
Pgp-substrate:	36.867122650146484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.619
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.168
CYP3A4-substrate:	0.434

ADMET: Excretion

Clearance (CL):	3.377
Half-life (T1/2):	0.822

ADMET: Toxicity

hERG Blockers:	0.099
Human Hepatotoxicity (H-HT):	0.923
Drug-inuced Liver Injury (DILI):	0.888
AMES Toxicity:	0.086
Rat Oral Acute Toxicity:	0.474
Maximum Recommended Daily Dose:	0.142
Skin Sensitization:	0.122
Carcinogencity:	0.154
Eye Corrosion:	0.005
Eye Irritation:	0.019
Respiratory Toxicity:	0.556

Download Data

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

Natural Product: NPC44538

Natural Product ID:	NPC44538
*Common Name:**	Klysimplexin E
IUPAC Name:	n.a.
Synonyms:	Klysimplexin E; Klysimplexins E
Standard InCHIKey:	DRGNCJVGVLURDB-CYRFFEBGSA-N
Standard InCHI:	InChI=1S/C24H38O7/c1-12(2)19-17(28)11-24(7,31-15(5)26)21-18-10-13(3)16(27)8-9-23(6,30-14(4)25)22(29-18)20(19)21/h12,16-22,27-28H,3,8-11H2,1-2,4-7H3/t16-,17+,18+,19-,20+,21+,22+,23+,24+/m0/s1
SMILES:	CC(=O)O[C@]1(C)CC[C@H](O)C(=C)C[C@H]2O[C@@H]1[C@@H]1[C@@H](C(C)C)[C@H](O)C[C@@]([C@H]21)(C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097090
PubChem CID:	44243660
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]
NPO32470	octocorallia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[21970540]
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	=	125000.0	nM	PMID[572881]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	7990427.22	nM	PMID[572881]

☑ 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 NPC44538 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	184
0.1-0.2	1636
0.2-0.3	5457
0.3-0.4	13656
0.4-0.5	9464
0.5-0.6	7644
0.6-0.7	4257
0.7-0.8	349
0.8-0.85	21
0.85-0.9	11
0.9-0.95	9
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC475684
0.9759	High Similarity	NPC291875
0.9639	High Similarity	NPC75443
0.9639	High Similarity	NPC92370
0.9639	High Similarity	NPC476723
0.9639	High Similarity	NPC476724
0.9639	High Similarity	NPC470260
0.9529	High Similarity	NPC91251
0.9524	High Similarity	NPC161560
0.9512	High Similarity	NPC471379
0.9512	High Similarity	NPC196911
0.9506	High Similarity	NPC5958
0.9259	High Similarity	NPC77003
0.9186	High Similarity	NPC312471
0.9186	High Similarity	NPC471378
0.9048	High Similarity	NPC476725
0.9036	High Similarity	NPC127917
0.9024	High Similarity	NPC118116
0.8864	High Similarity	NPC312805
0.8864	High Similarity	NPC122057
0.881	High Similarity	NPC239308
0.8721	High Similarity	NPC321812
0.8721	High Similarity	NPC322922
0.869	High Similarity	NPC103171
0.8652	High Similarity	NPC8729
0.8587	High Similarity	NPC111348
0.8571	High Similarity	NPC476720
0.8434	Intermediate Similarity	NPC43463
0.8434	Intermediate Similarity	NPC264610
0.8415	Intermediate Similarity	NPC136424
0.8415	Intermediate Similarity	NPC329626
0.8415	Intermediate Similarity	NPC293223
0.8404	Intermediate Similarity	NPC272223
0.8387	Intermediate Similarity	NPC473244
0.8351	Intermediate Similarity	NPC470263
0.8315	Intermediate Similarity	NPC309656
0.8295	Intermediate Similarity	NPC214315
0.8293	Intermediate Similarity	NPC36479
0.8242	Intermediate Similarity	NPC208839
0.8214	Intermediate Similarity	NPC252483
0.8214	Intermediate Similarity	NPC191345
0.8172	Intermediate Similarity	NPC241047
0.8152	Intermediate Similarity	NPC26046
0.814	Intermediate Similarity	NPC211049
0.8132	Intermediate Similarity	NPC123252
0.8132	Intermediate Similarity	NPC219937
0.8132	Intermediate Similarity	NPC153853
0.8132	Intermediate Similarity	NPC194485
0.8132	Intermediate Similarity	NPC53890
0.8095	Intermediate Similarity	NPC476719
0.8085	Intermediate Similarity	NPC471765
0.8085	Intermediate Similarity	NPC169270
0.8085	Intermediate Similarity	NPC292718
0.8085	Intermediate Similarity	NPC111834
0.8085	Intermediate Similarity	NPC221801
0.8085	Intermediate Similarity	NPC306797
0.8085	Intermediate Similarity	NPC211810
0.8085	Intermediate Similarity	NPC284194
0.8043	Intermediate Similarity	NPC219516
0.8043	Intermediate Similarity	NPC165180
0.8023	Intermediate Similarity	NPC186594
0.8022	Intermediate Similarity	NPC194642
0.8021	Intermediate Similarity	NPC38855
0.7979	Intermediate Similarity	NPC86893
0.7979	Intermediate Similarity	NPC292178
0.7978	Intermediate Similarity	NPC164424
0.7935	Intermediate Similarity	NPC10274
0.7931	Intermediate Similarity	NPC119922
0.7931	Intermediate Similarity	NPC116320
0.7912	Intermediate Similarity	NPC160304
0.7895	Intermediate Similarity	NPC284518
0.7872	Intermediate Similarity	NPC3359
0.7872	Intermediate Similarity	NPC476722
0.7872	Intermediate Similarity	NPC472360
0.7872	Intermediate Similarity	NPC472416
0.7865	Intermediate Similarity	NPC299963
0.7849	Intermediate Similarity	NPC41838
0.7849	Intermediate Similarity	NPC130840
0.7841	Intermediate Similarity	NPC216800
0.7835	Intermediate Similarity	NPC188968
0.7831	Intermediate Similarity	NPC476718
0.7826	Intermediate Similarity	NPC246028
0.7822	Intermediate Similarity	NPC38948
0.7812	Intermediate Similarity	NPC254121
0.7812	Intermediate Similarity	NPC274793
0.7812	Intermediate Similarity	NPC472998
0.7812	Intermediate Similarity	NPC473963
0.7812	Intermediate Similarity	NPC120446
0.7789	Intermediate Similarity	NPC276110
0.7789	Intermediate Similarity	NPC157686
0.7789	Intermediate Similarity	NPC259042
0.7778	Intermediate Similarity	NPC61442
0.7766	Intermediate Similarity	NPC147272
0.7755	Intermediate Similarity	NPC308824
0.7755	Intermediate Similarity	NPC144486
0.7755	Intermediate Similarity	NPC472554
0.7755	Intermediate Similarity	NPC49532
0.7745	Intermediate Similarity	NPC206618
0.7742	Intermediate Similarity	NPC48732
0.7742	Intermediate Similarity	NPC220216
0.7742	Intermediate Similarity	NPC209816
0.7732	Intermediate Similarity	NPC469725
0.7708	Intermediate Similarity	NPC472995
0.7708	Intermediate Similarity	NPC473964
0.7708	Intermediate Similarity	NPC129569
0.7708	Intermediate Similarity	NPC475304
0.7708	Intermediate Similarity	NPC93245
0.77	Intermediate Similarity	NPC473543
0.7684	Intermediate Similarity	NPC148000
0.7684	Intermediate Similarity	NPC24861
0.7684	Intermediate Similarity	NPC96736
0.7684	Intermediate Similarity	NPC476716
0.7684	Intermediate Similarity	NPC182826
0.7684	Intermediate Similarity	NPC225474
0.7684	Intermediate Similarity	NPC469596
0.7684	Intermediate Similarity	NPC178949
0.7684	Intermediate Similarity	NPC105375
0.7684	Intermediate Similarity	NPC39453
0.7677	Intermediate Similarity	NPC472552
0.7677	Intermediate Similarity	NPC31085
0.7667	Intermediate Similarity	NPC222634
0.7667	Intermediate Similarity	NPC102048
0.766	Intermediate Similarity	NPC473675
0.766	Intermediate Similarity	NPC124374
0.766	Intermediate Similarity	NPC249034
0.7653	Intermediate Similarity	NPC475877
0.764	Intermediate Similarity	NPC470155
0.764	Intermediate Similarity	NPC477446
0.764	Intermediate Similarity	NPC477447
0.764	Intermediate Similarity	NPC472504
0.7634	Intermediate Similarity	NPC261320
0.7629	Intermediate Similarity	NPC474395
0.7614	Intermediate Similarity	NPC472951
0.7614	Intermediate Similarity	NPC472943
0.7609	Intermediate Similarity	NPC166857
0.7609	Intermediate Similarity	NPC471377
0.7604	Intermediate Similarity	NPC469583
0.76	Intermediate Similarity	NPC475623
0.76	Intermediate Similarity	NPC475334
0.76	Intermediate Similarity	NPC473694
0.76	Intermediate Similarity	NPC473523
0.76	Intermediate Similarity	NPC471467
0.76	Intermediate Similarity	NPC72842
0.76	Intermediate Similarity	NPC156681
0.76	Intermediate Similarity	NPC99510
0.7596	Intermediate Similarity	NPC157476
0.7586	Intermediate Similarity	NPC52755
0.7582	Intermediate Similarity	NPC476715
0.7579	Intermediate Similarity	NPC99653
0.7576	Intermediate Similarity	NPC96784
0.7576	Intermediate Similarity	NPC98225
0.7576	Intermediate Similarity	NPC475617
0.7576	Intermediate Similarity	NPC235920
0.7573	Intermediate Similarity	NPC154906
0.7551	Intermediate Similarity	NPC470068
0.7551	Intermediate Similarity	NPC470066
0.7551	Intermediate Similarity	NPC477875
0.7551	Intermediate Similarity	NPC470067
0.7551	Intermediate Similarity	NPC477876
0.7549	Intermediate Similarity	NPC67321
0.7549	Intermediate Similarity	NPC187435
0.7549	Intermediate Similarity	NPC475781
0.7549	Intermediate Similarity	NPC471205
0.7529	Intermediate Similarity	NPC71152
0.7528	Intermediate Similarity	NPC470156
0.7528	Intermediate Similarity	NPC470154
0.7527	Intermediate Similarity	NPC263079
0.7527	Intermediate Similarity	NPC473436
0.7526	Intermediate Similarity	NPC472997
0.7526	Intermediate Similarity	NPC472996
0.7526	Intermediate Similarity	NPC256227
0.7526	Intermediate Similarity	NPC471903
0.7525	Intermediate Similarity	NPC181104
0.7525	Intermediate Similarity	NPC288502
0.7525	Intermediate Similarity	NPC475331
0.7525	Intermediate Similarity	NPC201144
0.7525	Intermediate Similarity	NPC475335
0.7525	Intermediate Similarity	NPC80809
0.7525	Intermediate Similarity	NPC103298
0.7525	Intermediate Similarity	NPC121518
0.75	Intermediate Similarity	NPC11956
0.75	Intermediate Similarity	NPC177701
0.75	Intermediate Similarity	NPC476367
0.75	Intermediate Similarity	NPC476471
0.75	Intermediate Similarity	NPC470972
0.75	Intermediate Similarity	NPC246347
0.75	Intermediate Similarity	NPC475344
0.75	Intermediate Similarity	NPC105490
0.75	Intermediate Similarity	NPC474922
0.75	Intermediate Similarity	NPC165578
0.75	Intermediate Similarity	NPC228593
0.75	Intermediate Similarity	NPC164551
0.75	Intermediate Similarity	NPC235196
0.75	Intermediate Similarity	NPC72755
0.75	Intermediate Similarity	NPC279260
0.7476	Intermediate Similarity	NPC472218
0.7476	Intermediate Similarity	NPC472217
0.7476	Intermediate Similarity	NPC472219
0.7476	Intermediate Similarity	NPC37628
0.7475	Intermediate Similarity	NPC477656

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 NPC44538 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	2275
0.2-0.3	3878
0.3-0.4	1963
0.4-0.5	500
0.5-0.6	286
0.6-0.7	75
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
0.7576	Intermediate Similarity	NPD5344	Discontinued
0.73	Intermediate Similarity	NPD6648	Approved
0.703	Intermediate Similarity	NPD4225	Approved
0.6961	Remote Similarity	NPD7640	Approved
0.6961	Remote Similarity	NPD7639	Approved
0.6915	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7524	Approved
0.6863	Remote Similarity	NPD7638	Approved
0.6822	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6695	Phase 3
0.6759	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7327	Approved
0.6726	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD3168	Discontinued
0.6667	Remote Similarity	NPD8133	Approved
0.66	Remote Similarity	NPD8034	Phase 2
0.66	Remote Similarity	NPD7637	Suspended
0.66	Remote Similarity	NPD8035	Phase 2
0.6591	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8335	Approved
0.6552	Remote Similarity	NPD8379	Approved
0.6552	Remote Similarity	NPD8378	Approved
0.6552	Remote Similarity	NPD8380	Approved
0.6552	Remote Similarity	NPD8033	Approved
0.6552	Remote Similarity	NPD8296	Approved
0.6545	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5778	Approved
0.6535	Remote Similarity	NPD5779	Approved
0.6531	Remote Similarity	NPD4250	Approved
0.6531	Remote Similarity	NPD7750	Discontinued
0.6531	Remote Similarity	NPD4251	Approved
0.6509	Remote Similarity	NPD7632	Discontinued
0.65	Remote Similarity	NPD6698	Approved
0.65	Remote Similarity	NPD7838	Discovery
0.65	Remote Similarity	NPD46	Approved
0.6495	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7525	Registered
0.6489	Remote Similarity	NPD6931	Approved
0.6489	Remote Similarity	NPD6930	Phase 2
0.6471	Remote Similarity	NPD371	Approved
0.6466	Remote Similarity	NPD8377	Approved
0.6466	Remote Similarity	NPD8294	Approved
0.6436	Remote Similarity	NPD7983	Approved
0.6429	Remote Similarity	NPD4249	Approved
0.6383	Remote Similarity	NPD6929	Approved
0.6373	Remote Similarity	NPD6399	Phase 3
0.6364	Remote Similarity	NPD6686	Approved
0.6355	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7115	Discovery
0.633	Remote Similarity	NPD6675	Approved
0.633	Remote Similarity	NPD5739	Approved
0.633	Remote Similarity	NPD7128	Approved
0.633	Remote Similarity	NPD6402	Approved
0.6316	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4820	Approved
0.6316	Remote Similarity	NPD4822	Approved
0.6316	Remote Similarity	NPD4821	Approved
0.6316	Remote Similarity	NPD4819	Approved
0.631	Remote Similarity	NPD1145	Discontinued
0.6306	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD8297	Approved
0.6275	Remote Similarity	NPD7087	Discontinued
0.6273	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD8517	Approved
0.6271	Remote Similarity	NPD7503	Approved
0.6271	Remote Similarity	NPD8515	Approved
0.6271	Remote Similarity	NPD8513	Phase 3
0.6271	Remote Similarity	NPD8516	Approved
0.625	Remote Similarity	NPD7492	Approved
0.6228	Remote Similarity	NPD4632	Approved
0.6226	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD7320	Approved
0.6216	Remote Similarity	NPD6881	Approved
0.6216	Remote Similarity	NPD6899	Approved
0.6211	Remote Similarity	NPD7645	Phase 2
0.6198	Remote Similarity	NPD7507	Approved
0.6198	Remote Similarity	NPD6616	Approved
0.6195	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6319	Approved
0.6186	Remote Similarity	NPD6054	Approved
0.6186	Remote Similarity	NPD6059	Approved
0.6182	Remote Similarity	NPD6008	Approved
0.6182	Remote Similarity	NPD5357	Phase 1
0.6179	Remote Similarity	NPD7319	Approved
0.617	Remote Similarity	NPD5776	Phase 2
0.617	Remote Similarity	NPD6925	Approved
0.6162	Remote Similarity	NPD6893	Approved
0.6161	Remote Similarity	NPD6373	Approved
0.6161	Remote Similarity	NPD6372	Approved
0.6154	Remote Similarity	NPD7748	Approved
0.6148	Remote Similarity	NPD7078	Approved
0.6148	Remote Similarity	NPD8293	Discontinued
0.6146	Remote Similarity	NPD7332	Phase 2
0.6146	Remote Similarity	NPD7514	Phase 3
0.614	Remote Similarity	NPD6053	Discontinued
0.6134	Remote Similarity	NPD6921	Approved
0.6132	Remote Similarity	NPD7902	Approved
0.6126	Remote Similarity	NPD5697	Approved
0.6126	Remote Similarity	NPD5701	Approved
0.6126	Remote Similarity	NPD6412	Phase 2
0.6126	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD3669	Approved
0.6122	Remote Similarity	NPD7154	Phase 3
0.6117	Remote Similarity	NPD7515	Phase 2
0.6106	Remote Similarity	NPD6883	Approved
0.6106	Remote Similarity	NPD7102	Approved
0.6106	Remote Similarity	NPD7290	Approved
0.6106	Remote Similarity	NPD6371	Approved
0.6105	Remote Similarity	NPD6114	Approved
0.6105	Remote Similarity	NPD4268	Approved
0.6105	Remote Similarity	NPD6697	Approved
0.6105	Remote Similarity	NPD4271	Approved
0.6105	Remote Similarity	NPD6118	Approved
0.6105	Remote Similarity	NPD6115	Approved
0.6105	Remote Similarity	NPD7145	Approved
0.6098	Remote Similarity	NPD7736	Approved
0.6083	Remote Similarity	NPD6370	Approved
0.6082	Remote Similarity	NPD6898	Phase 1
0.6078	Remote Similarity	NPD6101	Approved
0.6078	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6009	Approved
0.6068	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6649	Approved
0.6053	Remote Similarity	NPD6650	Approved
0.6053	Remote Similarity	NPD6869	Approved
0.6053	Remote Similarity	NPD6847	Approved
0.6053	Remote Similarity	NPD6617	Approved
0.6053	Remote Similarity	NPD8130	Phase 1
0.604	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD7604	Phase 2
0.6022	Remote Similarity	NPD1811	Approved
0.6022	Remote Similarity	NPD1810	Approved
0.6018	Remote Similarity	NPD6014	Approved
0.6018	Remote Similarity	NPD6012	Approved
0.6018	Remote Similarity	NPD6013	Approved
0.6016	Remote Similarity	NPD8074	Phase 3
0.6	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD6016	Approved
0.6	Remote Similarity	NPD6932	Approved
0.6	Remote Similarity	NPD6116	Phase 1
0.6	Remote Similarity	NPD5983	Phase 2
0.5981	Remote Similarity	NPD6084	Phase 2
0.5981	Remote Similarity	NPD6083	Phase 2
0.5963	Remote Similarity	NPD1700	Approved
0.5962	Remote Similarity	NPD6411	Approved
0.596	Remote Similarity	NPD5362	Discontinued
0.5957	Remote Similarity	NPD7339	Approved
0.5957	Remote Similarity	NPD6942	Approved
0.595	Remote Similarity	NPD5988	Approved
0.5935	Remote Similarity	NPD6336	Discontinued
0.5934	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6011	Approved
0.5922	Remote Similarity	NPD6051	Approved
0.5918	Remote Similarity	NPD6902	Approved
0.5913	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5211	Phase 2
0.5902	Remote Similarity	NPD8328	Phase 3
0.59	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4786	Approved
0.5895	Remote Similarity	NPD6933	Approved
0.5895	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD6117	Approved
0.5888	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD6683	Phase 2
0.5862	Remote Similarity	NPD368	Approved
0.5859	Remote Similarity	NPD6435	Approved
0.5859	Remote Similarity	NPD3667	Approved
0.5851	Remote Similarity	NPD6926	Approved
0.5851	Remote Similarity	NPD6924	Approved
0.5849	Remote Similarity	NPD7900	Approved
0.5849	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5282	Discontinued
0.5842	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4755	Approved
0.5818	Remote Similarity	NPD4159	Approved
0.5816	Remote Similarity	NPD7509	Discontinued
0.5816	Remote Similarity	NPD6928	Phase 2
0.5804	Remote Similarity	NPD5141	Approved
0.58	Remote Similarity	NPD5332	Approved
0.58	Remote Similarity	NPD5331	Approved
0.5794	Remote Similarity	NPD5695	Phase 3
0.5789	Remote Similarity	NPD8264	Approved
0.5784	Remote Similarity	NPD3618	Phase 1
0.5772	Remote Similarity	NPD6067	Discontinued
0.5769	Remote Similarity	NPD5328	Approved
0.5769	Remote Similarity	NPD1695	Approved
0.5758	Remote Similarity	NPD4790	Discontinued
0.5758	Remote Similarity	NPD5369	Approved
0.5755	Remote Similarity	NPD4202	Approved
0.5755	Remote Similarity	NPD8171	Discontinued
0.5741	Remote Similarity	NPD7839	Suspended
0.5727	Remote Similarity	NPD4700	Approved
0.5727	Remote Similarity	NPD5286	Approved
0.5727	Remote Similarity	NPD5285	Approved
0.5727	Remote Similarity	NPD4696	Approved
0.5714	Remote Similarity	NPD6274	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