NPASS Compound

Structure

NPC472791 OpenBabel07101718282D 31 36 0 0 1 0 0 0 0 0999 V2000 -0.7661 2.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9825 4.4376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9751 4.3299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2007 1.7728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.8952 2.9757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8261 3.3410 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8376 2.2070 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 4 29 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 7 1 0 0 0 0 6 18 2 0 0 0 0 7 19 2 0 0 0 0 8 12 1 0 0 0 0 8 21 1 0 0 0 0 9 13 1 0 0 0 0 9 20 1 0 0 0 0 10 25 1 0 0 0 0 12 24 1 0 0 0 0 13 26 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 27 1 0 0 0 0 16 30 1 0 0 0 0 17 19 1 0 0 0 0 18 28 1 0 0 0 0 19 31 1 0 0 0 0 20 24 1 0 0 0 0 20 27 1 0 0 0 0 21 25 1 0 0 0 0 21 27 1 0 0 0 0 22 24 1 0 0 0 0 22 26 1 0 0 0 0 23 25 1 6 0 0 0 23 29 1 0 0 0 0 23 30 1 0 0 0 0 24 1 1 6 0 0 0 25 2 1 6 0 0 0 26 3 1 6 0 0 0 26 31 1 0 0 0 0 27 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.28
Volume:	451.461
LogP:	4.972
LogD:	3.768
LogS:	-4.9
# Rotatable Bonds:	1
TPSA:	47.92
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.625
Synthetic Accessibility Score:	5.497
Fsp3:	0.778
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.013
MDCK Permeability:	2.4920505893533118e-05
Pgp-inhibitor:	0.721
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.764

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.274
Plasma Protein Binding (PPB):	96.81342315673828%
Volume Distribution (VD):	1.311
Pgp-substrate:	1.9705766439437866%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.884
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.888
CYP2C9-inhibitor:	0.179
CYP2C9-substrate:	0.126
CYP2D6-inhibitor:	0.766
CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.902
CYP3A4-substrate:	0.67

ADMET: Excretion

Clearance (CL):	14.618
Half-life (T1/2):	0.093

ADMET: Toxicity

hERG Blockers:	0.337
Human Hepatotoxicity (H-HT):	0.572
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.192
Maximum Recommended Daily Dose:	0.709
Skin Sensitization:	0.375
Carcinogencity:	0.212
Eye Corrosion:	0.003
Eye Irritation:	0.052
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC472791

Natural Product ID:	NPC472791
*Common Name:**	SQVROYDGAZNJQV-GNHJTJSWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SQVROYDGAZNJQV-GNHJTJSWSA-N
Standard InCHI:	InChI=1S/C27H38O4/c1-24-12-8-21-25(2)10-5-11-27(21,16-30-23(25)29-4)20(24)9-13-26(3)22(24)15-17-14-18(28)6-7-19(17)31-26/h6-7,14,20-23,28H,5,8-13,15-16H2,1-4H3/t20?,21?,22?,23-,24+,25-,26-,27-/m0/s1
SMILES:	CO[C@H]1OC[C@@]23C([C@]1(C)CCC2)CC[C@@]1(C3CC[C@]2(C1Cc1c(O2)ccc(c1)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586080
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350165]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	Okinawan, Japan	n.a.	PMID[14695804]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332859]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17407351]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[25987373]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7807132]
NPO24364	Petrosia corticata	Species	Petrosiidae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	6600.0	nM	PMID[552022]

☑ 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 NPC472791 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	457
0.1-0.2	1675
0.2-0.3	3576
0.3-0.4	8144
0.4-0.5	9323
0.5-0.6	8832
0.6-0.7	9076
0.7-0.8	1565
0.8-0.85	36
0.85-0.9	6
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472792
0.9776	High Similarity	NPC473049
0.9776	High Similarity	NPC472794
0.9328	High Similarity	NPC211352
0.9248	High Similarity	NPC473048
0.9179	High Similarity	NPC153019
0.9179	High Similarity	NPC473047
0.9098	High Similarity	NPC47288
0.8971	High Similarity	NPC289624
0.8971	High Similarity	NPC27578
0.8963	High Similarity	NPC472793
0.8811	High Similarity	NPC474599
0.8797	High Similarity	NPC248557
0.8662	High Similarity	NPC79372
0.8662	High Similarity	NPC76312
0.8592	High Similarity	NPC265335
0.8582	High Similarity	NPC474610
0.8571	High Similarity	NPC475839
0.8561	High Similarity	NPC321086
0.8467	Intermediate Similarity	NPC476452
0.8411	Intermediate Similarity	NPC200645
0.8411	Intermediate Similarity	NPC106669
0.8411	Intermediate Similarity	NPC475227
0.8406	Intermediate Similarity	NPC223912
0.8406	Intermediate Similarity	NPC176590
0.8403	Intermediate Similarity	NPC164743
0.8389	Intermediate Similarity	NPC44452
0.8367	Intermediate Similarity	NPC90645
0.8333	Intermediate Similarity	NPC183380
0.8333	Intermediate Similarity	NPC108164
0.8322	Intermediate Similarity	NPC475628
0.8288	Intermediate Similarity	NPC186033
0.8286	Intermediate Similarity	NPC325003
0.8267	Intermediate Similarity	NPC295573
0.8267	Intermediate Similarity	NPC470208
0.8261	Intermediate Similarity	NPC100414
0.8261	Intermediate Similarity	NPC128321
0.8261	Intermediate Similarity	NPC43000
0.8243	Intermediate Similarity	NPC23807
0.8243	Intermediate Similarity	NPC472457
0.8239	Intermediate Similarity	NPC138940
0.8224	Intermediate Similarity	NPC325860
0.8214	Intermediate Similarity	NPC97326
0.8209	Intermediate Similarity	NPC51341
0.82	Intermediate Similarity	NPC95990
0.8188	Intermediate Similarity	NPC471608
0.8182	Intermediate Similarity	NPC71372
0.8176	Intermediate Similarity	NPC133251
0.8176	Intermediate Similarity	NPC164183
0.8176	Intermediate Similarity	NPC253015
0.8176	Intermediate Similarity	NPC471065
0.8176	Intermediate Similarity	NPC96447
0.8169	Intermediate Similarity	NPC85595
0.8163	Intermediate Similarity	NPC323126
0.8162	Intermediate Similarity	NPC48623
0.8162	Intermediate Similarity	NPC168707
0.8156	Intermediate Similarity	NPC196193
0.8148	Intermediate Similarity	NPC474131
0.8129	Intermediate Similarity	NPC321822
0.8129	Intermediate Similarity	NPC325294
0.8125	Intermediate Similarity	NPC279463
0.8125	Intermediate Similarity	NPC137580
0.8121	Intermediate Similarity	NPC272619
0.8121	Intermediate Similarity	NPC286245
0.8116	Intermediate Similarity	NPC61685
0.8112	Intermediate Similarity	NPC24913
0.8112	Intermediate Similarity	NPC177712
0.8108	Intermediate Similarity	NPC472451
0.8105	Intermediate Similarity	NPC233467
0.8105	Intermediate Similarity	NPC59692
0.8099	Intermediate Similarity	NPC472590
0.8095	Intermediate Similarity	NPC5155
0.8092	Intermediate Similarity	NPC158784
0.8089	Intermediate Similarity	NPC100936
0.8089	Intermediate Similarity	NPC1253
0.8088	Intermediate Similarity	NPC45663
0.8085	Intermediate Similarity	NPC222108
0.8085	Intermediate Similarity	NPC96719
0.8082	Intermediate Similarity	NPC183781
0.8079	Intermediate Similarity	NPC212142
0.8079	Intermediate Similarity	NPC179809
0.8074	Intermediate Similarity	NPC471449
0.8074	Intermediate Similarity	NPC32152
0.8071	Intermediate Similarity	NPC186889
0.8069	Intermediate Similarity	NPC472800
0.806	Intermediate Similarity	NPC238176
0.806	Intermediate Similarity	NPC187993
0.8058	Intermediate Similarity	NPC133407
0.8058	Intermediate Similarity	NPC28476
0.8056	Intermediate Similarity	NPC473107
0.8043	Intermediate Similarity	NPC261992
0.8042	Intermediate Similarity	NPC472798
0.8039	Intermediate Similarity	NPC302915
0.8039	Intermediate Similarity	NPC259707
0.8039	Intermediate Similarity	NPC2745
0.8027	Intermediate Similarity	NPC193920
0.8027	Intermediate Similarity	NPC221134
0.8015	Intermediate Similarity	NPC232295
0.8014	Intermediate Similarity	NPC134260
0.8013	Intermediate Similarity	NPC275284
0.8013	Intermediate Similarity	NPC213074
0.8013	Intermediate Similarity	NPC15956
0.8013	Intermediate Similarity	NPC114505
0.8013	Intermediate Similarity	NPC193473
0.8013	Intermediate Similarity	NPC224674
0.8013	Intermediate Similarity	NPC31325
0.8	Intermediate Similarity	NPC271076
0.8	Intermediate Similarity	NPC476301
0.8	Intermediate Similarity	NPC43508
0.8	Intermediate Similarity	NPC79957
0.7987	Intermediate Similarity	NPC157783
0.7987	Intermediate Similarity	NPC21902
0.7986	Intermediate Similarity	NPC77196
0.7986	Intermediate Similarity	NPC469610
0.7985	Intermediate Similarity	NPC69539
0.7985	Intermediate Similarity	NPC141001
0.7974	Intermediate Similarity	NPC469706
0.7974	Intermediate Similarity	NPC145979
0.7974	Intermediate Similarity	NPC469707
0.7974	Intermediate Similarity	NPC182368
0.7974	Intermediate Similarity	NPC225815
0.7974	Intermediate Similarity	NPC98624
0.7974	Intermediate Similarity	NPC218041
0.7974	Intermediate Similarity	NPC214326
0.7974	Intermediate Similarity	NPC260781
0.7974	Intermediate Similarity	NPC185955
0.7974	Intermediate Similarity	NPC195561
0.7974	Intermediate Similarity	NPC9933
0.7973	Intermediate Similarity	NPC210192
0.7972	Intermediate Similarity	NPC244888
0.7972	Intermediate Similarity	NPC118683
0.7972	Intermediate Similarity	NPC258073
0.7972	Intermediate Similarity	NPC211413
0.7972	Intermediate Similarity	NPC164804
0.7972	Intermediate Similarity	NPC284232
0.7972	Intermediate Similarity	NPC68205
0.7972	Intermediate Similarity	NPC293203
0.7971	Intermediate Similarity	NPC46586
0.7971	Intermediate Similarity	NPC204535
0.7971	Intermediate Similarity	NPC188997
0.7961	Intermediate Similarity	NPC290902
0.7961	Intermediate Similarity	NPC159697
0.7961	Intermediate Similarity	NPC117788
0.7961	Intermediate Similarity	NPC130959
0.7961	Intermediate Similarity	NPC474795
0.7961	Intermediate Similarity	NPC291326
0.7961	Intermediate Similarity	NPC474834
0.7961	Intermediate Similarity	NPC474940
0.7961	Intermediate Similarity	NPC303013
0.7961	Intermediate Similarity	NPC474856
0.7959	Intermediate Similarity	NPC472151
0.7958	Intermediate Similarity	NPC93962
0.7958	Intermediate Similarity	NPC472797
0.7947	Intermediate Similarity	NPC155564
0.7947	Intermediate Similarity	NPC102280
0.7947	Intermediate Similarity	NPC248053
0.7945	Intermediate Similarity	NPC471522
0.7943	Intermediate Similarity	NPC473134
0.7937	Intermediate Similarity	NPC25889
0.7935	Intermediate Similarity	NPC78809
0.7933	Intermediate Similarity	NPC470235
0.7933	Intermediate Similarity	NPC471667
0.7933	Intermediate Similarity	NPC225445
0.7933	Intermediate Similarity	NPC151704
0.7933	Intermediate Similarity	NPC79429
0.7933	Intermediate Similarity	NPC129417
0.7933	Intermediate Similarity	NPC472155
0.7933	Intermediate Similarity	NPC217635
0.7933	Intermediate Similarity	NPC283995
0.7931	Intermediate Similarity	NPC476615
0.7931	Intermediate Similarity	NPC476617
0.7931	Intermediate Similarity	NPC476616
0.7929	Intermediate Similarity	NPC252962
0.7919	Intermediate Similarity	NPC472353
0.7917	Intermediate Similarity	NPC469611
0.7917	Intermediate Similarity	NPC51262
0.7914	Intermediate Similarity	NPC474130
0.7911	Intermediate Similarity	NPC185231
0.7908	Intermediate Similarity	NPC474893
0.7908	Intermediate Similarity	NPC475940
0.7908	Intermediate Similarity	NPC220006
0.7908	Intermediate Similarity	NPC181452
0.7905	Intermediate Similarity	NPC106944
0.7902	Intermediate Similarity	NPC249425
0.7895	Intermediate Similarity	NPC473480
0.7895	Intermediate Similarity	NPC15538
0.7895	Intermediate Similarity	NPC227902
0.7891	Intermediate Similarity	NPC304152
0.7891	Intermediate Similarity	NPC262328
0.7891	Intermediate Similarity	NPC470308
0.7891	Intermediate Similarity	NPC470307
0.7891	Intermediate Similarity	NPC87777
0.7887	Intermediate Similarity	NPC53986
0.7887	Intermediate Similarity	NPC38664
0.7887	Intermediate Similarity	NPC40377
0.7885	Intermediate Similarity	NPC159922
0.7883	Intermediate Similarity	NPC135467
0.7883	Intermediate Similarity	NPC260832
0.7881	Intermediate Similarity	NPC173630
0.7881	Intermediate Similarity	NPC307466

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 NPC472791 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	911
0.2-0.3	1721
0.3-0.4	2800
0.4-0.5	1827
0.5-0.6	1058
0.6-0.7	413
0.7-0.8	41
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
0.8095	Intermediate Similarity	NPD6674	Discontinued
0.8071	Intermediate Similarity	NPD2861	Phase 2
0.8045	Intermediate Similarity	NPD6671	Approved
0.8028	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD6696	Suspended
0.7902	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD4908	Phase 1
0.7755	Intermediate Similarity	NPD7097	Phase 1
0.7721	Intermediate Similarity	NPD7340	Approved
0.7708	Intermediate Similarity	NPD4625	Phase 3
0.766	Intermediate Similarity	NPD4749	Approved
0.766	Intermediate Similarity	NPD5327	Phase 3
0.7619	Intermediate Similarity	NPD5735	Approved
0.7568	Intermediate Similarity	NPD6353	Approved
0.7551	Intermediate Similarity	NPD4060	Phase 1
0.7551	Intermediate Similarity	NPD4140	Approved
0.7547	Intermediate Similarity	NPD8455	Phase 2
0.7533	Intermediate Similarity	NPD6100	Approved
0.7533	Intermediate Similarity	NPD6099	Approved
0.7518	Intermediate Similarity	NPD1091	Approved
0.7518	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD1398	Phase 1
0.75	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD3496	Discontinued
0.7413	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD8313	Approved
0.7412	Intermediate Similarity	NPD8312	Approved
0.7405	Intermediate Similarity	NPD7458	Discontinued
0.7386	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4624	Approved
0.7372	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7228	Approved
0.7361	Intermediate Similarity	NPD8651	Approved
0.7351	Intermediate Similarity	NPD4108	Discontinued
0.7347	Intermediate Similarity	NPD7095	Approved
0.7285	Intermediate Similarity	NPD7119	Phase 2
0.7273	Intermediate Similarity	NPD1611	Approved
0.7266	Intermediate Similarity	NPD7157	Approved
0.7255	Intermediate Similarity	NPD5763	Approved
0.7255	Intermediate Similarity	NPD5762	Approved
0.7254	Intermediate Similarity	NPD1778	Approved
0.7239	Intermediate Similarity	NPD968	Approved
0.7219	Intermediate Similarity	NPD4097	Suspended
0.7216	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7037	Approved
0.72	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3620	Phase 2
0.72	Intermediate Similarity	NPD1613	Approved
0.7174	Intermediate Similarity	NPD7635	Approved
0.7163	Intermediate Similarity	NPD7644	Approved
0.7162	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3705	Approved
0.7152	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6584	Phase 3
0.7143	Intermediate Similarity	NPD7266	Discontinued
0.7133	Intermediate Similarity	NPD8032	Phase 2
0.7133	Intermediate Similarity	NPD4626	Approved
0.7126	Intermediate Similarity	NPD3787	Discontinued
0.7125	Intermediate Similarity	NPD1653	Approved
0.7117	Intermediate Similarity	NPD5929	Approved
0.7115	Intermediate Similarity	NPD8166	Discontinued
0.7115	Intermediate Similarity	NPD7003	Approved
0.7113	Intermediate Similarity	NPD3091	Approved
0.7113	Intermediate Similarity	NPD1548	Phase 1
0.7107	Intermediate Similarity	NPD6090	Discontinued
0.7107	Intermediate Similarity	NPD6273	Approved
0.7103	Intermediate Similarity	NPD2230	Approved
0.7103	Intermediate Similarity	NPD2233	Approved
0.7103	Intermediate Similarity	NPD2232	Approved
0.7095	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5736	Approved
0.7089	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7041	Phase 2
0.7076	Intermediate Similarity	NPD7074	Phase 3
0.7075	Intermediate Similarity	NPD3094	Phase 2
0.7067	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7985	Registered
0.7066	Intermediate Similarity	NPD8127	Discontinued
0.7066	Intermediate Similarity	NPD6959	Discontinued
0.7063	Intermediate Similarity	NPD5691	Approved
0.7063	Intermediate Similarity	NPD5585	Approved
0.7055	Intermediate Similarity	NPD37	Approved
0.7048	Intermediate Similarity	NPD6234	Discontinued
0.7044	Intermediate Similarity	NPD7447	Phase 1
0.7039	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5124	Phase 1
0.7034	Intermediate Similarity	NPD3092	Approved
0.703	Intermediate Similarity	NPD4965	Approved
0.703	Intermediate Similarity	NPD4967	Phase 2
0.703	Intermediate Similarity	NPD4966	Approved
0.7025	Intermediate Similarity	NPD5058	Phase 3
0.7018	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7054	Approved
0.6994	Remote Similarity	NPD7240	Approved
0.6992	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7472	Approved
0.6975	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2238	Phase 2
0.6957	Remote Similarity	NPD4727	Phase 1
0.6954	Remote Similarity	NPD7294	Phase 1
0.6944	Remote Similarity	NPD1357	Approved
0.6939	Remote Similarity	NPD6582	Phase 2
0.6939	Remote Similarity	NPD6583	Phase 3
0.6933	Remote Similarity	NPD7028	Phase 2
0.6932	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1138	Approved
0.6929	Remote Similarity	NPD7843	Approved
0.6929	Remote Similarity	NPD5535	Approved
0.6928	Remote Similarity	NPD6355	Discontinued
0.6919	Remote Similarity	NPD7698	Approved
0.6919	Remote Similarity	NPD5844	Phase 1
0.6919	Remote Similarity	NPD7697	Approved
0.6919	Remote Similarity	NPD7696	Phase 3
0.6914	Remote Similarity	NPD7310	Approved
0.6914	Remote Similarity	NPD7312	Approved
0.6914	Remote Similarity	NPD7311	Approved
0.6914	Remote Similarity	NPD7313	Approved
0.691	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6663	Approved
0.6901	Remote Similarity	NPD6387	Discontinued
0.6901	Remote Similarity	NPD709	Approved
0.6897	Remote Similarity	NPD3095	Discontinued
0.6897	Remote Similarity	NPD4059	Approved
0.6897	Remote Similarity	NPD7251	Discontinued
0.6887	Remote Similarity	NPD3027	Phase 3
0.6886	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7833	Phase 2
0.6886	Remote Similarity	NPD7831	Phase 2
0.6884	Remote Similarity	NPD2684	Approved
0.6879	Remote Similarity	NPD5283	Phase 1
0.6875	Remote Similarity	NPD7741	Discontinued
0.6875	Remote Similarity	NPD7309	Approved
0.6875	Remote Similarity	NPD7213	Phase 3
0.6875	Remote Similarity	NPD7212	Phase 2
0.6871	Remote Similarity	NPD1608	Approved
0.6871	Remote Similarity	NPD2231	Phase 2
0.6871	Remote Similarity	NPD2235	Phase 2
0.6867	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2237	Approved
0.6865	Remote Similarity	NPD6823	Phase 2
0.6864	Remote Similarity	NPD7199	Phase 2
0.686	Remote Similarity	NPD3751	Discontinued
0.6859	Remote Similarity	NPD2935	Discontinued
0.6857	Remote Similarity	NPD1139	Approved
0.6857	Remote Similarity	NPD1137	Approved
0.6857	Remote Similarity	NPD7808	Phase 3
0.6854	Remote Similarity	NPD7906	Approved
0.6848	Remote Similarity	NPD6782	Approved
0.6848	Remote Similarity	NPD6779	Approved
0.6848	Remote Similarity	NPD6777	Approved
0.6848	Remote Similarity	NPD5722	Discontinued
0.6848	Remote Similarity	NPD6776	Approved
0.6848	Remote Similarity	NPD6780	Approved
0.6848	Remote Similarity	NPD6778	Approved
0.6848	Remote Similarity	NPD6781	Approved
0.6846	Remote Similarity	NPD2797	Approved
0.6842	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6798	Discontinued
0.6839	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6797	Phase 2
0.6835	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7435	Discontinued
0.6826	Remote Similarity	NPD7768	Phase 2
0.6826	Remote Similarity	NPD7773	Phase 2
0.6824	Remote Similarity	NPD3051	Approved
0.6824	Remote Similarity	NPD4359	Approved
0.6824	Remote Similarity	NPD3685	Discontinued
0.6815	Remote Similarity	NPD7030	Discontinued
0.6815	Remote Similarity	NPD2346	Discontinued
0.6813	Remote Similarity	NPD6666	Approved
0.6813	Remote Similarity	NPD6667	Approved
0.6807	Remote Similarity	NPD7819	Suspended
0.68	Remote Similarity	NPD6559	Discontinued
0.6798	Remote Similarity	NPD4663	Approved
0.6797	Remote Similarity	NPD6233	Phase 2
0.6795	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7033	Discontinued
0.6792	Remote Similarity	NPD4110	Phase 3
0.6792	Remote Similarity	NPD4628	Phase 3
0.6792	Remote Similarity	NPD7466	Approved
0.6792	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7870	Phase 2
0.6791	Remote Similarity	NPD7871	Phase 2
0.6784	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD2970	Approved
0.6784	Remote Similarity	NPD2969	Approved
0.6781	Remote Similarity	NPD5126	Approved
0.6781	Remote Similarity	NPD3019	Approved
0.6781	Remote Similarity	NPD5125	Phase 3
0.6779	Remote Similarity	NPD1283	Approved
0.6774	Remote Similarity	NPD2157	Approved
0.6772	Remote Similarity	NPD7701	Phase 2
0.677	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3226	Approved
0.6761	Remote Similarity	NPD7549	Discontinued

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