NPASS Compound

Structure

NPC470929 OpenBabel07101719122D 31 35 0 0 1 0 0 0 0 0999 V2000 -4.5671 -5.0547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2300 -4.5144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6061 -2.5942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6047 -4.4251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5976 -3.3250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6146 -1.8980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9432 -3.1345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2677 -3.8847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5617 -1.8980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9683 -1.0813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3631 -0.8885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7403 -2.4028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1339 -2.9075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4889 -1.3933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7403 0.6258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1339 0.1210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4889 0.6258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2426 -4.3045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9306 -3.3444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2802 -3.6748 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3631 0.1210 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9683 -2.7147 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0082 -1.3933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7403 -1.3933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0082 -2.4028 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6146 -0.8885 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6146 0.1210 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1339 -0.8885 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2374 0.6258 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7782 0.4493 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 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 2 0 0 0 0 6 26 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 17 21 1 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 20 4 1 6 0 0 0 20 22 1 0 0 0 0 21 29 1 1 0 0 0 22 25 1 1 0 0 0 23 25 1 1 0 0 0 23 28 1 0 0 0 0 24 26 1 1 0 0 0 24 28 1 0 0 0 0 25 5 1 1 0 0 0 26 27 1 1 0 0 0 27 15 1 1 0 0 0 27 30 1 0 0 0 0 28 16 1 1 0 0 0 28 31 1 0 0 0 0 30 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.34
Volume:	473.796
LogP:	5.71
LogD:	5.219
LogS:	-5.587
# Rotatable Bonds:	5
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.383
Synthetic Accessibility Score:	6.4
Fsp3:	0.929
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.989
MDCK Permeability:	4.5497505198e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.06
30% Bioavailability (F30%):	0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	97.56488800048828%
Volume Distribution (VD):	1.237
Pgp-substrate:	2.3112454414367676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.77
CYP2C19-inhibitor:	0.127
CYP2C19-substrate:	0.959
CYP2C9-inhibitor:	0.287
CYP2C9-substrate:	0.316
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.906
CYP3A4-inhibitor:	0.835
CYP3A4-substrate:	0.778

ADMET: Excretion

Clearance (CL):	9.42
Half-life (T1/2):	0.175

ADMET: Toxicity

hERG Blockers:	0.622
Human Hepatotoxicity (H-HT):	0.574
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.332
Skin Sensitization:	0.603
Carcinogencity:	0.028
Eye Corrosion:	0.83
Eye Irritation:	0.592
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC470929

Natural Product ID:	NPC470929
*Common Name:**	OQLLJRFUGICFKK-WBIZBJRUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OQLLJRFUGICFKK-WBIZBJRUSA-N
Standard InCHI:	InChI=1S/C28H46O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h18,20-24,29H,3,7-17H2,1-2,4-6H3/t20-,21+,22-,23-,24-,25-,26-,27-,28+/m1/s1
SMILES:	CC(C)C(=C)CCC(C)C1CCC2C1(CCC3C24CCC5(C3(CCC(C5)O)C)OO4)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2322188
PubChem CID:	71720444
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids

*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
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121250]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	Hainan soft coral	n.a.	PMID[23357636]
NPO17094	Sinularia depressa	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC50	=	500000.0	nM	PMID[484378]

☑ 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 NPC470929 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	234
0.1-0.2	2715
0.2-0.3	10503
0.3-0.4	14613
0.4-0.5	5692
0.5-0.6	4196
0.6-0.7	3597
0.7-0.8	1069
0.8-0.85	54
0.85-0.9	18
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9359	High Similarity	NPC475679
0.9351	High Similarity	NPC31828
0.9231	High Similarity	NPC475727
0.9231	High Similarity	NPC116119
0.9231	High Similarity	NPC472742
0.9231	High Similarity	NPC80297
0.9012	High Similarity	NPC211135
0.9012	High Similarity	NPC85095
0.9012	High Similarity	NPC232023
0.9012	High Similarity	NPC216420
0.8974	High Similarity	NPC202540
0.8961	High Similarity	NPC3403
0.8902	High Similarity	NPC86238
0.8861	High Similarity	NPC477819
0.8861	High Similarity	NPC477817
0.8846	High Similarity	NPC78067
0.8846	High Similarity	NPC14112
0.8846	High Similarity	NPC278091
0.8846	High Similarity	NPC93662
0.8846	High Similarity	NPC86305
0.8831	High Similarity	NPC472503
0.8831	High Similarity	NPC308440
0.8824	High Similarity	NPC101886
0.875	High Similarity	NPC49627
0.875	High Similarity	NPC49599
0.8718	High Similarity	NPC240235
0.8718	High Similarity	NPC104387
0.8718	High Similarity	NPC178383
0.8718	High Similarity	NPC231256
0.8718	High Similarity	NPC212879
0.8706	High Similarity	NPC212596
0.8706	High Similarity	NPC4574
0.869	High Similarity	NPC121981
0.869	High Similarity	NPC201273
0.8642	High Similarity	NPC71535
0.8642	High Similarity	NPC78545
0.8625	High Similarity	NPC301707
0.8625	High Similarity	NPC42853
0.8608	High Similarity	NPC91573
0.859	High Similarity	NPC192638
0.859	High Similarity	NPC25511
0.859	High Similarity	NPC62657
0.8588	High Similarity	NPC304083
0.8571	High Similarity	NPC111234
0.8554	High Similarity	NPC113978
0.8519	High Similarity	NPC24504
0.8519	High Similarity	NPC476316
0.8519	High Similarity	NPC80530
0.8519	High Similarity	NPC273410
0.8506	High Similarity	NPC270511
0.8506	High Similarity	NPC14380
0.8506	High Similarity	NPC470390
0.8506	High Similarity	NPC192437
0.8506	High Similarity	NPC245410
0.85	High Similarity	NPC119355
0.85	High Similarity	NPC212241
0.85	High Similarity	NPC248830
0.8488	Intermediate Similarity	NPC473436
0.8488	Intermediate Similarity	NPC475605
0.8481	Intermediate Similarity	NPC185536
0.8481	Intermediate Similarity	NPC70982
0.8481	Intermediate Similarity	NPC230704
0.8481	Intermediate Similarity	NPC103822
0.8471	Intermediate Similarity	NPC6605
0.8452	Intermediate Similarity	NPC256567
0.8452	Intermediate Similarity	NPC255882
0.8442	Intermediate Similarity	NPC45296
0.8415	Intermediate Similarity	NPC47149
0.8415	Intermediate Similarity	NPC236237
0.8415	Intermediate Similarity	NPC102253
0.8415	Intermediate Similarity	NPC322313
0.8395	Intermediate Similarity	NPC244385
0.8395	Intermediate Similarity	NPC138621
0.8395	Intermediate Similarity	NPC472499
0.8395	Intermediate Similarity	NPC472342
0.8395	Intermediate Similarity	NPC475
0.8395	Intermediate Similarity	NPC6978
0.8395	Intermediate Similarity	NPC472502
0.8395	Intermediate Similarity	NPC285761
0.8395	Intermediate Similarity	NPC472501
0.8395	Intermediate Similarity	NPC472500
0.8395	Intermediate Similarity	NPC167037
0.8395	Intermediate Similarity	NPC102708
0.8391	Intermediate Similarity	NPC74258
0.8391	Intermediate Similarity	NPC138974
0.8375	Intermediate Similarity	NPC63958
0.8372	Intermediate Similarity	NPC477600
0.8354	Intermediate Similarity	NPC196358
0.8354	Intermediate Similarity	NPC145552
0.8354	Intermediate Similarity	NPC5046
0.8354	Intermediate Similarity	NPC49168
0.8354	Intermediate Similarity	NPC254509
0.8333	Intermediate Similarity	NPC477818
0.8333	Intermediate Similarity	NPC110778
0.8313	Intermediate Similarity	NPC470383
0.8295	Intermediate Similarity	NPC10274
0.8272	Intermediate Similarity	NPC331618
0.8272	Intermediate Similarity	NPC138502
0.8272	Intermediate Similarity	NPC307336
0.8272	Intermediate Similarity	NPC257191
0.8272	Intermediate Similarity	NPC260301
0.8256	Intermediate Similarity	NPC269058
0.8256	Intermediate Similarity	NPC299068
0.8256	Intermediate Similarity	NPC24277
0.8256	Intermediate Similarity	NPC71520
0.825	Intermediate Similarity	NPC200243
0.8235	Intermediate Similarity	NPC209802
0.8228	Intermediate Similarity	NPC195489
0.8214	Intermediate Similarity	NPC248886
0.8202	Intermediate Similarity	NPC219516
0.8193	Intermediate Similarity	NPC13554
0.8182	Intermediate Similarity	NPC470361
0.8182	Intermediate Similarity	NPC109744
0.8148	Intermediate Similarity	NPC237460
0.8148	Intermediate Similarity	NPC38141
0.814	Intermediate Similarity	NPC470360
0.8125	Intermediate Similarity	NPC192501
0.8125	Intermediate Similarity	NPC304499
0.8125	Intermediate Similarity	NPC476736
0.8125	Intermediate Similarity	NPC10476
0.8125	Intermediate Similarity	NPC228994
0.8118	Intermediate Similarity	NPC141941
0.8118	Intermediate Similarity	NPC207013
0.8118	Intermediate Similarity	NPC193870
0.8101	Intermediate Similarity	NPC127094
0.8095	Intermediate Similarity	NPC157655
0.8095	Intermediate Similarity	NPC242350
0.809	Intermediate Similarity	NPC11216
0.809	Intermediate Similarity	NPC204188
0.809	Intermediate Similarity	NPC46758
0.809	Intermediate Similarity	NPC329596
0.809	Intermediate Similarity	NPC3345
0.809	Intermediate Similarity	NPC475751
0.809	Intermediate Similarity	NPC473956
0.809	Intermediate Similarity	NPC80561
0.809	Intermediate Similarity	NPC291484
0.8077	Intermediate Similarity	NPC66407
0.8077	Intermediate Similarity	NPC254037
0.8077	Intermediate Similarity	NPC129829
0.8072	Intermediate Similarity	NPC5604
0.8072	Intermediate Similarity	NPC472463
0.8052	Intermediate Similarity	NPC185874
0.8052	Intermediate Similarity	NPC253303
0.8052	Intermediate Similarity	NPC269077
0.8052	Intermediate Similarity	NPC139207
0.8046	Intermediate Similarity	NPC6391
0.8043	Intermediate Similarity	NPC472989
0.8025	Intermediate Similarity	NPC243027
0.8025	Intermediate Similarity	NPC196136
0.8025	Intermediate Similarity	NPC158208
0.8023	Intermediate Similarity	NPC299963
0.8023	Intermediate Similarity	NPC475798
0.8023	Intermediate Similarity	NPC474493
0.8023	Intermediate Similarity	NPC124172
0.8023	Intermediate Similarity	NPC127606
0.8	Intermediate Similarity	NPC97404
0.8	Intermediate Similarity	NPC296701
0.8	Intermediate Similarity	NPC30166
0.8	Intermediate Similarity	NPC228049
0.8	Intermediate Similarity	NPC41554
0.8	Intermediate Similarity	NPC52585
0.8	Intermediate Similarity	NPC68630
0.8	Intermediate Similarity	NPC218616
0.8	Intermediate Similarity	NPC472504
0.8	Intermediate Similarity	NPC211009
0.7978	Intermediate Similarity	NPC105495
0.7976	Intermediate Similarity	NPC206735
0.7975	Intermediate Similarity	NPC192192
0.7975	Intermediate Similarity	NPC282454
0.7975	Intermediate Similarity	NPC283316
0.7957	Intermediate Similarity	NPC476893
0.7955	Intermediate Similarity	NPC186145
0.7955	Intermediate Similarity	NPC474657
0.7952	Intermediate Similarity	NPC147993
0.7952	Intermediate Similarity	NPC65897
0.7952	Intermediate Similarity	NPC85346
0.7952	Intermediate Similarity	NPC87604
0.7952	Intermediate Similarity	NPC302041
0.7949	Intermediate Similarity	NPC472741
0.7927	Intermediate Similarity	NPC470766
0.7927	Intermediate Similarity	NPC73875
0.7927	Intermediate Similarity	NPC189883
0.7907	Intermediate Similarity	NPC134481
0.7907	Intermediate Similarity	NPC5280
0.7907	Intermediate Similarity	NPC475726
0.7907	Intermediate Similarity	NPC472743
0.7907	Intermediate Similarity	NPC246956
0.7889	Intermediate Similarity	NPC123252
0.7889	Intermediate Similarity	NPC53890
0.7889	Intermediate Similarity	NPC194485
0.7889	Intermediate Similarity	NPC219937
0.7875	Intermediate Similarity	NPC1340
0.7875	Intermediate Similarity	NPC301226
0.7875	Intermediate Similarity	NPC157422
0.7875	Intermediate Similarity	NPC100586
0.7875	Intermediate Similarity	NPC109457
0.7875	Intermediate Similarity	NPC252182
0.7875	Intermediate Similarity	NPC470071
0.7875	Intermediate Similarity	NPC187471
0.7872	Intermediate Similarity	NPC476895

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 NPC470929 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	3057
0.2-0.3	4115
0.3-0.4	1187
0.4-0.5	229
0.5-0.6	194
0.6-0.7	128
0.7-0.8	13
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
0.8415	Intermediate Similarity	NPD7525	Registered
0.7727	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7645	Phase 2
0.7625	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7339	Approved
0.759	Intermediate Similarity	NPD6942	Approved
0.7558	Intermediate Similarity	NPD6930	Phase 2
0.7558	Intermediate Similarity	NPD6931	Approved
0.7442	Intermediate Similarity	NPD6929	Approved
0.7416	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6932	Approved
0.7303	Intermediate Similarity	NPD6695	Phase 3
0.7294	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6924	Approved
0.7262	Intermediate Similarity	NPD6926	Approved
0.7241	Intermediate Similarity	NPD6683	Phase 2
0.7234	Intermediate Similarity	NPD8035	Phase 2
0.7234	Intermediate Similarity	NPD8034	Phase 2
0.7209	Intermediate Similarity	NPD6925	Approved
0.7209	Intermediate Similarity	NPD5776	Phase 2
0.7174	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6928	Phase 2
0.7159	Intermediate Similarity	NPD7514	Phase 3
0.7143	Intermediate Similarity	NPD6893	Approved
0.7126	Intermediate Similarity	NPD7145	Approved
0.7111	Intermediate Similarity	NPD4788	Approved
0.7108	Intermediate Similarity	NPD4787	Phase 1
0.7093	Intermediate Similarity	NPD6933	Approved
0.7033	Intermediate Similarity	NPD4786	Approved
0.7024	Intermediate Similarity	NPD4243	Approved
0.7021	Intermediate Similarity	NPD5328	Approved
0.6989	Remote Similarity	NPD7750	Discontinued
0.6989	Remote Similarity	NPD7524	Approved
0.6979	Remote Similarity	NPD4202	Approved
0.6972	Remote Similarity	NPD7328	Approved
0.6972	Remote Similarity	NPD7327	Approved
0.6966	Remote Similarity	NPD4748	Discontinued
0.6966	Remote Similarity	NPD7509	Discontinued
0.6966	Remote Similarity	NPD7332	Phase 2
0.6932	Remote Similarity	NPD6697	Approved
0.6932	Remote Similarity	NPD6118	Approved
0.6932	Remote Similarity	NPD6115	Approved
0.6932	Remote Similarity	NPD6114	Approved
0.6909	Remote Similarity	NPD7516	Approved
0.6889	Remote Similarity	NPD6902	Approved
0.6889	Remote Similarity	NPD6898	Phase 1
0.6882	Remote Similarity	NPD3618	Phase 1
0.6875	Remote Similarity	NPD6079	Approved
0.6869	Remote Similarity	NPD4755	Approved
0.686	Remote Similarity	NPD4784	Approved
0.686	Remote Similarity	NPD4785	Approved
0.6824	Remote Similarity	NPD7151	Approved
0.6824	Remote Similarity	NPD7152	Approved
0.6824	Remote Similarity	NPD7150	Approved
0.6824	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6116	Phase 1
0.6813	Remote Similarity	NPD3667	Approved
0.68	Remote Similarity	NPD7638	Approved
0.6786	Remote Similarity	NPD6923	Approved
0.6786	Remote Similarity	NPD6922	Approved
0.6782	Remote Similarity	NPD3703	Phase 2
0.6733	Remote Similarity	NPD7639	Approved
0.6733	Remote Similarity	NPD7640	Approved
0.6733	Remote Similarity	NPD4700	Approved
0.6733	Remote Similarity	NPD5285	Approved
0.6733	Remote Similarity	NPD4696	Approved
0.6733	Remote Similarity	NPD5286	Approved
0.6706	Remote Similarity	NPD7144	Approved
0.6706	Remote Similarity	NPD7143	Approved
0.6705	Remote Similarity	NPD6117	Approved
0.6701	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD8378	Approved
0.6637	Remote Similarity	NPD8379	Approved
0.6637	Remote Similarity	NPD8335	Approved
0.6637	Remote Similarity	NPD8296	Approved
0.6637	Remote Similarity	NPD8380	Approved
0.6606	Remote Similarity	NPD8133	Approved
0.6602	Remote Similarity	NPD5211	Phase 2
0.6602	Remote Similarity	NPD5225	Approved
0.6602	Remote Similarity	NPD5226	Approved
0.6602	Remote Similarity	NPD5224	Approved
0.6602	Remote Similarity	NPD4633	Approved
0.6591	Remote Similarity	NPD4190	Phase 3
0.6591	Remote Similarity	NPD5275	Approved
0.6588	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7128	Approved
0.6571	Remote Similarity	NPD6675	Approved
0.6571	Remote Similarity	NPD6402	Approved
0.6571	Remote Similarity	NPD5739	Approved
0.6549	Remote Similarity	NPD8294	Approved
0.6549	Remote Similarity	NPD8377	Approved
0.6538	Remote Similarity	NPD5174	Approved
0.6538	Remote Similarity	NPD5175	Approved
0.6531	Remote Similarity	NPD7515	Phase 2
0.6505	Remote Similarity	NPD5223	Approved
0.6495	Remote Similarity	NPD4753	Phase 2
0.6491	Remote Similarity	NPD8033	Approved
0.6489	Remote Similarity	NPD3666	Approved
0.6489	Remote Similarity	NPD3133	Approved
0.6489	Remote Similarity	NPD3665	Phase 1
0.6484	Remote Similarity	NPD4195	Approved
0.6481	Remote Similarity	NPD4634	Approved
0.6476	Remote Similarity	NPD5141	Approved
0.6471	Remote Similarity	NPD5360	Phase 3
0.6471	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6399	Phase 3
0.6465	Remote Similarity	NPD8171	Discontinued
0.6449	Remote Similarity	NPD6881	Approved
0.6449	Remote Similarity	NPD7320	Approved
0.6449	Remote Similarity	NPD6899	Approved
0.6436	Remote Similarity	NPD4697	Phase 3
0.6436	Remote Similarity	NPD5222	Approved
0.6436	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5221	Approved
0.6415	Remote Similarity	NPD4767	Approved
0.6415	Remote Similarity	NPD4768	Approved
0.6389	Remote Similarity	NPD6372	Approved
0.6389	Remote Similarity	NPD6373	Approved
0.6386	Remote Similarity	NPD371	Approved
0.6381	Remote Similarity	NPD4754	Approved
0.6374	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5173	Approved
0.6355	Remote Similarity	NPD5697	Approved
0.6355	Remote Similarity	NPD6412	Phase 2
0.6355	Remote Similarity	NPD5701	Approved
0.633	Remote Similarity	NPD7290	Approved
0.633	Remote Similarity	NPD7102	Approved
0.633	Remote Similarity	NPD6883	Approved
0.6322	Remote Similarity	NPD4245	Approved
0.6322	Remote Similarity	NPD4789	Approved
0.6322	Remote Similarity	NPD4244	Approved
0.6296	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4730	Approved
0.6296	Remote Similarity	NPD4729	Approved
0.6296	Remote Similarity	NPD5128	Approved
0.6286	Remote Similarity	NPD7632	Discontinued
0.6277	Remote Similarity	NPD4223	Phase 3
0.6277	Remote Similarity	NPD4221	Approved
0.6273	Remote Similarity	NPD6650	Approved
0.6273	Remote Similarity	NPD6847	Approved
0.6273	Remote Similarity	NPD6649	Approved
0.6273	Remote Similarity	NPD6869	Approved
0.6273	Remote Similarity	NPD8130	Phase 1
0.6273	Remote Similarity	NPD6617	Approved
0.6271	Remote Similarity	NPD7507	Approved
0.625	Remote Similarity	NPD5329	Approved
0.625	Remote Similarity	NPD7319	Approved
0.6239	Remote Similarity	NPD6012	Approved
0.6239	Remote Similarity	NPD6014	Approved
0.6239	Remote Similarity	NPD6013	Approved
0.6238	Remote Similarity	NPD7748	Approved
0.6216	Remote Similarity	NPD6882	Approved
0.6216	Remote Similarity	NPD8297	Approved
0.6214	Remote Similarity	NPD6083	Phase 2
0.6214	Remote Similarity	NPD6084	Phase 2
0.6214	Remote Similarity	NPD7902	Approved
0.6207	Remote Similarity	NPD3698	Phase 2
0.6207	Remote Similarity	NPD7503	Approved
0.62	Remote Similarity	NPD7637	Suspended
0.619	Remote Similarity	NPD4159	Approved
0.6186	Remote Similarity	NPD5279	Phase 3
0.6182	Remote Similarity	NPD5249	Phase 3
0.6182	Remote Similarity	NPD5248	Approved
0.6182	Remote Similarity	NPD5247	Approved
0.6182	Remote Similarity	NPD5250	Approved
0.6182	Remote Similarity	NPD5251	Approved
0.6176	Remote Similarity	NPD4629	Approved
0.6176	Remote Similarity	NPD5210	Approved
0.6161	Remote Similarity	NPD4632	Approved
0.6154	Remote Similarity	NPD5290	Discontinued
0.6147	Remote Similarity	NPD6011	Approved
0.6146	Remote Similarity	NPD4197	Approved
0.6146	Remote Similarity	NPD3668	Phase 3
0.6126	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5217	Approved
0.6126	Remote Similarity	NPD5215	Approved
0.6126	Remote Similarity	NPD5216	Approved
0.6121	Remote Similarity	NPD6054	Approved
0.6121	Remote Similarity	NPD6059	Approved
0.6118	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6700	Approved
0.61	Remote Similarity	NPD7136	Phase 2
0.6091	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD4758	Discontinued
0.6061	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD8264	Approved
0.604	Remote Similarity	NPD6702	Approved
0.604	Remote Similarity	NPD6703	Approved
0.6036	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD5135	Approved
0.6036	Remote Similarity	NPD5169	Approved
0.6033	Remote Similarity	NPD7736	Approved
0.6022	Remote Similarity	NPD3671	Phase 1
0.602	Remote Similarity	NPD4690	Approved
0.602	Remote Similarity	NPD4689	Approved
0.602	Remote Similarity	NPD4693	Phase 3

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