NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	894.46
Volume:	898.288
LogP:	4.54
LogD:	2.944
LogS:	-5.434
# Rotatable Bonds:	15
TPSA:	240.11
# H-Bond Aceptor:	17
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.126
Synthetic Accessibility Score:	7.845
Fsp3:	0.761
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.268
MDCK Permeability:	0.00021009343618061393
Pgp-inhibitor:	0.401
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.062
20% Bioavailability (F20%):	0.513
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	73.99054718017578%
Volume Distribution (VD):	0.66
Pgp-substrate:	7.7468366622924805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.36
CYP2C9-inhibitor:	0.31
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.015
CYP3A4-inhibitor:	0.89
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	2.762
Half-life (T1/2):	0.557

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.929
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.252
Rat Oral Acute Toxicity:	0.687
Maximum Recommended Daily Dose:	1.0
Skin Sensitization:	0.94
Carcinogencity:	0.073
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.672

Download Data

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

Natural Product: NPC476740

Natural Product ID:	NPC476740
*Common Name:**	[(1S,3S,5Z,7R,8E,11S,12S,13E,15R,17R,21R,23R,25S)-12-butanoyloxy-1,11,21-trihydroxy-17-[(1R)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-25-yl] 3-methylbutanoate
IUPAC Name:	[(1S,3S,5Z,7R,8E,11S,12S,13E,15R,17R,21R,23R,25S)-12-butanoyloxy-1,11,21-trihydroxy-17-[(1R)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-25-yl] 3-methylbutanoate
Synonyms:	Bryostatin 4
Standard InCHIKey:	OUVYQBNLDHLZNW-OIVDDIEPSA-N
Standard InCHI:	InChI=1S/C46H70O17/c1-11-12-37(49)61-42-29(20-39(51)57-10)19-32-23-35(27(4)47)59-41(53)22-30(48)21-33-24-36(60-40(52)15-26(2)3)44(7,8)45(54,62-33)25-34-17-28(18-38(50)56-9)16-31(58-34)13-14-43(5,6)46(42,55)63-32/h13-14,18,20,26-27,30-36,42,47-48,54-55H,11-12,15-17,19,21-25H2,1-10H3/b14-13+,28-18+,29-20+/t27-,30-,31+,32-,33-,34+,35-,36+,42+,45+,46-/m1/s1
SMILES:	CCCC(=O)O[C@H]1/C(=C/C(=O)OC)/C[C@@H]2C[C@@H](OC(=O)C[C@@H](C[C@@H]3C[C@@H](C([C@@](O3)(C[C@@H]4C/C(=C/C(=O)OC)/C[C@@H](O4)/C=C/C([C@@]1(O2)O)(C)C)O)(C)C)OC(=O)CC(C)C)O)[C@@H](C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44559608
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

*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
NPO11979	Bugula neritina	Species	Bugulidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ja00388a092]
NPO11979	Bugula neritina	Species	Bugulidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[25932671]
NPO11979	Bugula neritina	Species	Bugulidae	Eukaryota	n.a.	Gulf of Aomori, Japan	n.a.	PMID[8691208]
NPO11979	Bugula neritina	Species	Bugulidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882431]
NPO11979	Bugula neritina	Species	Bugulidae	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
Others	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	Activity	=	62	%	PMID[3734809]

☑ 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 NPC476740 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	224
0.1-0.2	1244
0.2-0.3	3961
0.3-0.4	7153
0.4-0.5	12931
0.5-0.6	8928
0.6-0.7	6304
0.7-0.8	1884
0.8-0.85	57
0.85-0.9	1
0.9-0.95	2
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476738
0.9794	High Similarity	NPC474581
0.9794	High Similarity	NPC309398
0.9794	High Similarity	NPC473816
0.9794	High Similarity	NPC475367
0.96	High Similarity	NPC193765
0.9216	High Similarity	NPC473807
0.8585	High Similarity	NPC315836
0.8585	High Similarity	NPC313668
0.8431	Intermediate Similarity	NPC255592
0.8431	Intermediate Similarity	NPC83895
0.8431	Intermediate Similarity	NPC261377
0.8431	Intermediate Similarity	NPC187761
0.8431	Intermediate Similarity	NPC308567
0.8381	Intermediate Similarity	NPC472748
0.8365	Intermediate Similarity	NPC473596
0.8333	Intermediate Similarity	NPC40812
0.8302	Intermediate Similarity	NPC472751
0.8302	Intermediate Similarity	NPC472749
0.8286	Intermediate Similarity	NPC472747
0.8286	Intermediate Similarity	NPC472750
0.8235	Intermediate Similarity	NPC255410
0.8235	Intermediate Similarity	NPC143446
0.8218	Intermediate Similarity	NPC71589
0.8208	Intermediate Similarity	NPC469869
0.819	Intermediate Similarity	NPC472754
0.819	Intermediate Similarity	NPC313569
0.8165	Intermediate Similarity	NPC83005
0.8155	Intermediate Similarity	NPC120299
0.8142	Intermediate Similarity	NPC13710
0.8137	Intermediate Similarity	NPC300710
0.8119	Intermediate Similarity	NPC320089
0.81	Intermediate Similarity	NPC313670
0.8095	Intermediate Similarity	NPC2313
0.8095	Intermediate Similarity	NPC154132
0.8095	Intermediate Similarity	NPC475655
0.8095	Intermediate Similarity	NPC472753
0.8095	Intermediate Similarity	NPC57586
0.8095	Intermediate Similarity	NPC475157
0.8095	Intermediate Similarity	NPC471637
0.8087	Intermediate Similarity	NPC470829
0.8087	Intermediate Similarity	NPC473228
0.8077	Intermediate Similarity	NPC475653
0.8058	Intermediate Similarity	NPC475540
0.8058	Intermediate Similarity	NPC475525
0.8058	Intermediate Similarity	NPC476066
0.8058	Intermediate Similarity	NPC473765
0.8058	Intermediate Similarity	NPC473605
0.8058	Intermediate Similarity	NPC475593
0.8058	Intermediate Similarity	NPC475241
0.8058	Intermediate Similarity	NPC475164
0.8058	Intermediate Similarity	NPC475375
0.8039	Intermediate Similarity	NPC472198
0.8039	Intermediate Similarity	NPC159698
0.8037	Intermediate Similarity	NPC231271
0.8037	Intermediate Similarity	NPC470519
0.802	Intermediate Similarity	NPC470379
0.802	Intermediate Similarity	NPC470373
0.802	Intermediate Similarity	NPC472199
0.8	Intermediate Similarity	NPC48692
0.8	Intermediate Similarity	NPC476127
0.8	Intermediate Similarity	NPC476150
0.7982	Intermediate Similarity	NPC219900
0.7982	Intermediate Similarity	NPC392
0.7982	Intermediate Similarity	NPC177524
0.7981	Intermediate Similarity	NPC475332
0.7946	Intermediate Similarity	NPC75167
0.7946	Intermediate Similarity	NPC311592
0.7944	Intermediate Similarity	NPC197736
0.7944	Intermediate Similarity	NPC472755
0.7941	Intermediate Similarity	NPC478037
0.7941	Intermediate Similarity	NPC238090
0.7941	Intermediate Similarity	NPC478036
0.7941	Intermediate Similarity	NPC472195
0.7941	Intermediate Similarity	NPC472196
0.7931	Intermediate Similarity	NPC170880
0.7931	Intermediate Similarity	NPC469812
0.7931	Intermediate Similarity	NPC476204
0.7931	Intermediate Similarity	NPC183353
0.7931	Intermediate Similarity	NPC170084
0.7928	Intermediate Similarity	NPC126897
0.7928	Intermediate Similarity	NPC297945
0.7917	Intermediate Similarity	NPC470912
0.7913	Intermediate Similarity	NPC473839
0.7913	Intermediate Similarity	NPC77689
0.7913	Intermediate Similarity	NPC473636
0.7913	Intermediate Similarity	NPC211093
0.7905	Intermediate Similarity	NPC40182
0.7905	Intermediate Similarity	NPC161855
0.7905	Intermediate Similarity	NPC198422
0.7895	Intermediate Similarity	NPC474483
0.7895	Intermediate Similarity	NPC473968
0.7881	Intermediate Similarity	NPC318135
0.7876	Intermediate Similarity	NPC181145
0.787	Intermediate Similarity	NPC203659
0.787	Intermediate Similarity	NPC472756
0.7869	Intermediate Similarity	NPC225791
0.7864	Intermediate Similarity	NPC294293
0.7864	Intermediate Similarity	NPC477345
0.7864	Intermediate Similarity	NPC477348
0.7864	Intermediate Similarity	NPC238264
0.7851	Intermediate Similarity	NPC477197
0.785	Intermediate Similarity	NPC201191
0.7843	Intermediate Similarity	NPC472197
0.7843	Intermediate Similarity	NPC476075
0.7843	Intermediate Similarity	NPC476084
0.7833	Intermediate Similarity	NPC472269
0.7833	Intermediate Similarity	NPC477078
0.7833	Intermediate Similarity	NPC112492
0.7833	Intermediate Similarity	NPC472270
0.7833	Intermediate Similarity	NPC329923
0.7833	Intermediate Similarity	NPC477075
0.7833	Intermediate Similarity	NPC23020
0.7833	Intermediate Similarity	NPC245094
0.7833	Intermediate Similarity	NPC472268
0.7833	Intermediate Similarity	NPC475281
0.7826	Intermediate Similarity	NPC475309
0.7826	Intermediate Similarity	NPC109603
0.7826	Intermediate Similarity	NPC93688
0.781	Intermediate Similarity	NPC266842
0.781	Intermediate Similarity	NPC278506
0.7807	Intermediate Similarity	NPC44170
0.78	Intermediate Similarity	NPC477959
0.78	Intermediate Similarity	NPC199382
0.78	Intermediate Similarity	NPC86005
0.7798	Intermediate Similarity	NPC315070
0.7788	Intermediate Similarity	NPC36954
0.7787	Intermediate Similarity	NPC277212
0.7787	Intermediate Similarity	NPC312650
0.7787	Intermediate Similarity	NPC71391
0.7787	Intermediate Similarity	NPC192765
0.7787	Intermediate Similarity	NPC473918
0.7787	Intermediate Similarity	NPC178264
0.7787	Intermediate Similarity	NPC46823
0.7787	Intermediate Similarity	NPC30279
0.7787	Intermediate Similarity	NPC476776
0.7778	Intermediate Similarity	NPC110989
0.7778	Intermediate Similarity	NPC4620
0.7778	Intermediate Similarity	NPC471494
0.7769	Intermediate Similarity	NPC47995
0.7769	Intermediate Similarity	NPC1314
0.7769	Intermediate Similarity	NPC97918
0.7769	Intermediate Similarity	NPC477196
0.7769	Intermediate Similarity	NPC88311
0.7769	Intermediate Similarity	NPC82380
0.7769	Intermediate Similarity	NPC477076
0.7769	Intermediate Similarity	NPC107536
0.7769	Intermediate Similarity	NPC477079
0.7769	Intermediate Similarity	NPC252289
0.7769	Intermediate Similarity	NPC9470
0.7769	Intermediate Similarity	NPC252657
0.7769	Intermediate Similarity	NPC470913
0.7769	Intermediate Similarity	NPC472267
0.7769	Intermediate Similarity	NPC141600
0.7769	Intermediate Similarity	NPC11577
0.7769	Intermediate Similarity	NPC269484
0.7769	Intermediate Similarity	NPC280029
0.7769	Intermediate Similarity	NPC470518
0.7769	Intermediate Similarity	NPC273878
0.7769	Intermediate Similarity	NPC115656
0.7769	Intermediate Similarity	NPC265841
0.7769	Intermediate Similarity	NPC477077
0.7769	Intermediate Similarity	NPC244296
0.7769	Intermediate Similarity	NPC305793
0.7767	Intermediate Similarity	NPC159092
0.7767	Intermediate Similarity	NPC476300
0.7759	Intermediate Similarity	NPC475775
0.7759	Intermediate Similarity	NPC476529
0.7759	Intermediate Similarity	NPC67917
0.7759	Intermediate Similarity	NPC314268
0.7759	Intermediate Similarity	NPC313802
0.7759	Intermediate Similarity	NPC477515
0.7757	Intermediate Similarity	NPC476611
0.775	Intermediate Similarity	NPC470516
0.7742	Intermediate Similarity	NPC279915
0.7742	Intermediate Similarity	NPC110700
0.7739	Intermediate Similarity	NPC475809
0.7739	Intermediate Similarity	NPC134430
0.7736	Intermediate Similarity	NPC56071
0.7736	Intermediate Similarity	NPC70733
0.7731	Intermediate Similarity	NPC470922
0.7724	Intermediate Similarity	NPC476779
0.7719	Intermediate Similarity	NPC110861
0.7714	Intermediate Similarity	NPC473291
0.7714	Intermediate Similarity	NPC195645
0.7714	Intermediate Similarity	NPC165332
0.7714	Intermediate Similarity	NPC180722
0.7706	Intermediate Similarity	NPC220964
0.7706	Intermediate Similarity	NPC475676
0.7705	Intermediate Similarity	NPC476074
0.7705	Intermediate Similarity	NPC476780
0.7705	Intermediate Similarity	NPC173435
0.7705	Intermediate Similarity	NPC475167
0.7705	Intermediate Similarity	NPC134914
0.7705	Intermediate Similarity	NPC271610
0.7705	Intermediate Similarity	NPC478065
0.7705	Intermediate Similarity	NPC300655
0.7705	Intermediate Similarity	NPC476775
0.7705	Intermediate Similarity	NPC262796
0.7705	Intermediate Similarity	NPC475377

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 NPC476740 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	1481
0.2-0.3	3536
0.3-0.4	2462
0.4-0.5	944
0.5-0.6	369
0.6-0.7	128
0.7-0.8	32
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8283	Intermediate Similarity	NPD46	Approved
0.8283	Intermediate Similarity	NPD6698	Approved
0.82	Intermediate Similarity	NPD7983	Approved
0.7982	Intermediate Similarity	NPD6686	Approved
0.7931	Intermediate Similarity	NPD8513	Phase 3
0.7931	Intermediate Similarity	NPD8515	Approved
0.7931	Intermediate Similarity	NPD8516	Approved
0.7931	Intermediate Similarity	NPD8517	Approved
0.7928	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7839	Suspended
0.7647	Intermediate Similarity	NPD7830	Approved
0.7647	Intermediate Similarity	NPD7829	Approved
0.7573	Intermediate Similarity	NPD7838	Discovery
0.75	Intermediate Similarity	NPD8328	Phase 3
0.7459	Intermediate Similarity	NPD8074	Phase 3
0.7339	Intermediate Similarity	NPD7319	Approved
0.7333	Intermediate Similarity	NPD8444	Approved
0.7333	Intermediate Similarity	NPD6411	Approved
0.7317	Intermediate Similarity	NPD8448	Approved
0.728	Intermediate Similarity	NPD8390	Approved
0.728	Intermediate Similarity	NPD8391	Approved
0.728	Intermediate Similarity	NPD8392	Approved
0.7264	Intermediate Similarity	NPD5779	Approved
0.7264	Intermediate Similarity	NPD5778	Approved
0.7257	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7507	Approved
0.7236	Intermediate Similarity	NPD8451	Approved
0.7217	Intermediate Similarity	NPD6371	Approved
0.7179	Intermediate Similarity	NPD8133	Approved
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7642	Approved
0.7043	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8340	Approved
0.7016	Intermediate Similarity	NPD8342	Approved
0.7016	Intermediate Similarity	NPD8341	Approved
0.7016	Intermediate Similarity	NPD8299	Approved
0.6967	Remote Similarity	NPD8377	Approved
0.6967	Remote Similarity	NPD8294	Approved
0.6957	Remote Similarity	NPD6412	Phase 2
0.6937	Remote Similarity	NPD4225	Approved
0.6916	Remote Similarity	NPD5785	Approved
0.6911	Remote Similarity	NPD8378	Approved
0.6911	Remote Similarity	NPD8033	Approved
0.6911	Remote Similarity	NPD8380	Approved
0.6911	Remote Similarity	NPD8379	Approved
0.6911	Remote Similarity	NPD8335	Approved
0.6911	Remote Similarity	NPD8296	Approved
0.686	Remote Similarity	NPD7115	Discovery
0.6829	Remote Similarity	NPD6319	Approved
0.6818	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6053	Discontinued
0.6803	Remote Similarity	NPD7641	Discontinued
0.6794	Remote Similarity	NPD8415	Approved
0.6786	Remote Similarity	NPD7638	Approved
0.6746	Remote Similarity	NPD7492	Approved
0.6742	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5282	Discontinued
0.6726	Remote Similarity	NPD7640	Approved
0.6726	Remote Similarity	NPD7639	Approved
0.6721	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8080	Discontinued
0.6719	Remote Similarity	NPD7736	Approved
0.6697	Remote Similarity	NPD7637	Suspended
0.6695	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6054	Approved
0.6693	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD8293	Discontinued
0.6641	Remote Similarity	NPD7078	Approved
0.664	Remote Similarity	NPD8268	Approved
0.664	Remote Similarity	NPD8266	Approved
0.664	Remote Similarity	NPD8267	Approved
0.664	Remote Similarity	NPD8269	Approved
0.664	Remote Similarity	NPD7503	Approved
0.6613	Remote Similarity	NPD7516	Approved
0.6604	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6370	Approved
0.6571	Remote Similarity	NPD7154	Phase 3
0.6565	Remote Similarity	NPD7260	Phase 2
0.6562	Remote Similarity	NPD8273	Phase 1
0.656	Remote Similarity	NPD6059	Approved
0.6542	Remote Similarity	NPD5786	Approved
0.6529	Remote Similarity	NPD6882	Approved
0.6508	Remote Similarity	NPD6015	Approved
0.6508	Remote Similarity	NPD6921	Approved
0.6508	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6016	Approved
0.65	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6435	Approved
0.6475	Remote Similarity	NPD4632	Approved
0.6457	Remote Similarity	NPD5988	Approved
0.6452	Remote Similarity	NPD6009	Approved
0.6452	Remote Similarity	NPD7500	Approved
0.6449	Remote Similarity	NPD5363	Approved
0.6436	Remote Similarity	NPD8039	Approved
0.6333	Remote Similarity	NPD6881	Approved
0.6333	Remote Similarity	NPD6899	Approved
0.633	Remote Similarity	NPD4251	Approved
0.633	Remote Similarity	NPD4250	Approved
0.6321	Remote Similarity	NPD4269	Approved
0.6321	Remote Similarity	NPD4270	Approved
0.6321	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD8130	Phase 1
0.6311	Remote Similarity	NPD6649	Approved
0.6311	Remote Similarity	NPD6650	Approved
0.6303	Remote Similarity	NPD5739	Approved
0.6303	Remote Similarity	NPD6402	Approved
0.6303	Remote Similarity	NPD6675	Approved
0.6303	Remote Similarity	NPD7128	Approved
0.6293	Remote Similarity	NPD6648	Approved
0.6286	Remote Similarity	NPD5368	Approved
0.6286	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7748	Approved
0.6281	Remote Similarity	NPD6372	Approved
0.6281	Remote Similarity	NPD6373	Approved
0.6262	Remote Similarity	NPD5362	Discontinued
0.6261	Remote Similarity	NPD7902	Approved
0.6259	Remote Similarity	NPD8384	Approved
0.625	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4249	Approved
0.623	Remote Similarity	NPD7102	Approved
0.623	Remote Similarity	NPD7290	Approved
0.623	Remote Similarity	NPD4634	Approved
0.623	Remote Similarity	NPD6883	Approved
0.623	Remote Similarity	NPD6421	Discontinued
0.6226	Remote Similarity	NPD5369	Approved
0.6198	Remote Similarity	NPD7320	Approved
0.6195	Remote Similarity	NPD6399	Phase 3
0.6186	Remote Similarity	NPD7632	Discontinued
0.6179	Remote Similarity	NPD6869	Approved
0.6179	Remote Similarity	NPD6847	Approved
0.6179	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6617	Approved
0.6168	Remote Similarity	NPD5209	Approved
0.6154	Remote Similarity	NPD7604	Phase 2
0.6148	Remote Similarity	NPD6012	Approved
0.6148	Remote Similarity	NPD6845	Suspended
0.6148	Remote Similarity	NPD6013	Approved
0.6148	Remote Similarity	NPD6014	Approved
0.6147	Remote Similarity	NPD1694	Approved
0.6132	Remote Similarity	NPD4822	Approved
0.6132	Remote Similarity	NPD4820	Approved
0.6132	Remote Similarity	NPD4252	Approved
0.6132	Remote Similarity	NPD4819	Approved
0.6132	Remote Similarity	NPD4821	Approved
0.6124	Remote Similarity	NPD5983	Phase 2
0.6121	Remote Similarity	NPD6084	Phase 2
0.6121	Remote Similarity	NPD6083	Phase 2
0.6116	Remote Similarity	NPD5701	Approved
0.6111	Remote Similarity	NPD6110	Phase 1
0.6106	Remote Similarity	NPD7515	Phase 2
0.6095	Remote Similarity	NPD4271	Approved
0.6095	Remote Similarity	NPD4268	Approved
0.6091	Remote Similarity	NPD6422	Discontinued
0.609	Remote Similarity	NPD8336	Approved
0.609	Remote Similarity	NPD6033	Approved
0.609	Remote Similarity	NPD8337	Approved
0.6066	Remote Similarity	NPD6011	Approved
0.6061	Remote Similarity	NPD6336	Discontinued
0.605	Remote Similarity	NPD8083	Approved
0.605	Remote Similarity	NPD8138	Approved
0.605	Remote Similarity	NPD8084	Approved
0.605	Remote Similarity	NPD8086	Approved
0.605	Remote Similarity	NPD8082	Approved
0.605	Remote Similarity	NPD8085	Approved
0.605	Remote Similarity	NPD8139	Approved
0.6038	Remote Similarity	NPD7329	Approved
0.6033	Remote Similarity	NPD8393	Approved
0.6033	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8275	Approved
0.6	Remote Similarity	NPD8276	Approved
0.6	Remote Similarity	NPD7900	Approved
0.6	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6079	Approved
0.595	Remote Similarity	NPD8081	Approved
0.595	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD5695	Phase 3
0.5946	Remote Similarity	NPD5330	Approved
0.5946	Remote Similarity	NPD7334	Approved
0.5946	Remote Similarity	NPD6684	Approved
0.5946	Remote Similarity	NPD7521	Approved
0.5946	Remote Similarity	NPD7146	Approved
0.5946	Remote Similarity	NPD6409	Approved
0.5929	Remote Similarity	NPD1695	Approved
0.5929	Remote Similarity	NPD5328	Approved
0.592	Remote Similarity	NPD6401	Clinical (unspecified phase)

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