NPASS Compound

Structure

NPC74137 OpenBabel07101718322D 24 25 0 0 1 0 0 0 0 0999 V2000 -6.8510 0.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0758 -0.6387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0567 -1.9836 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 -0.7355 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4368 -0.8282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5391 -0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4028 -1.0870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7297 -1.5353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5050 -0.3105 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 -1.8320 -0.7588 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1099 -0.3799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7638 -1.2765 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 2.5981 -0.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 12 1 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 10 17 2 0 0 0 0 11 13 2 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 22 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 18 20 1 0 0 0 0 19 23 1 0 0 0 0 20 21 2 0 0 0 0 21 24 1 0 0 0 0 22 5 1 6 0 0 0 22 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.22
Volume:	373.717
LogP:	6.449
LogD:	5.221
LogS:	-5.69
# Rotatable Bonds:	6
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.618
Synthetic Accessibility Score:	3.595
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.848
MDCK Permeability:	2.3882950699771754e-05
Pgp-inhibitor:	0.886
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.416

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.337
Plasma Protein Binding (PPB):	100.0064926147461%
Volume Distribution (VD):	4.932
Pgp-substrate:	1.5158123970031738%

ADMET: Metabolism

CYP1A2-inhibitor:	0.94
CYP1A2-substrate:	0.332
CYP2C19-inhibitor:	0.76
CYP2C19-substrate:	0.761
CYP2C9-inhibitor:	0.711
CYP2C9-substrate:	0.953
CYP2D6-inhibitor:	0.966
CYP2D6-substrate:	0.615
CYP3A4-inhibitor:	0.92
CYP3A4-substrate:	0.252

ADMET: Excretion

Clearance (CL):	10.155
Half-life (T1/2):	0.295

ADMET: Toxicity

hERG Blockers:	0.457
Human Hepatotoxicity (H-HT):	0.953
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.862
Skin Sensitization:	0.951
Carcinogencity:	0.081
Eye Corrosion:	0.011
Eye Irritation:	0.873
Respiratory Toxicity:	0.421

Download Data

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

Natural Product: NPC74137

Natural Product ID:	NPC74137
*Common Name:**	Albatrelin C
IUPAC Name:	(2R)-2-[(3E)-4,8-dimethylnona-3,7-dienyl]-2,5-dimethylchromen-7-ol
Synonyms:	Albatrelin C
Standard InCHIKey:	QJCFVYYUAJZBKT-IHSQGBLNSA-N
Standard InCHI:	InChI=1S/C22H30O2/c1-16(2)8-6-9-17(3)10-7-12-22(5)13-11-20-18(4)14-19(23)15-21(20)24-22/h8,10-11,13-15,23H,6-7,9,12H2,1-5H3/b17-10+/t22-/m1/s1
SMILES:	C/C(=CCC[C@]1(C)C=Cc2c(O1)cc(cc2C)O)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332227
PubChem CID:	71524350
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO10941	Albatrellus ovinus	Species	Albatrellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23305465]
NPO10941	Albatrellus ovinus	Species	Albatrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10941	Albatrellus ovinus	Species	Albatrellaceae	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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[492850]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[492850]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[492850]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	40000.0	nM	PMID[492850]

☑ 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 NPC74137 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	385
0.1-0.2	1804
0.2-0.3	4967
0.3-0.4	13391
0.4-0.5	4417
0.5-0.6	4531
0.6-0.7	8383
0.7-0.8	4106
0.8-0.85	574
0.85-0.9	123
0.9-0.95	15
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9322	High Similarity	NPC102639
0.9322	High Similarity	NPC218753
0.9316	High Similarity	NPC137294
0.9316	High Similarity	NPC85895
0.9262	High Similarity	NPC46978
0.9174	High Similarity	NPC270030
0.9083	High Similarity	NPC212965
0.9048	High Similarity	NPC469611
0.9008	High Similarity	NPC120638
0.8976	High Similarity	NPC469610
0.8968	High Similarity	NPC160623
0.8968	High Similarity	NPC8899
0.8968	High Similarity	NPC469907
0.896	High Similarity	NPC16577
0.8943	High Similarity	NPC131397
0.8943	High Similarity	NPC476254
0.8943	High Similarity	NPC113495
0.8943	High Similarity	NPC105031
0.8934	High Similarity	NPC96940
0.8871	High Similarity	NPC170485
0.8852	High Similarity	NPC57199
0.8846	High Similarity	NPC35550
0.8833	High Similarity	NPC295259
0.8824	High Similarity	NPC33270
0.8824	High Similarity	NPC474933
0.8824	High Similarity	NPC69261
0.8814	High Similarity	NPC185541
0.8814	High Similarity	NPC464
0.881	High Similarity	NPC222108
0.881	High Similarity	NPC96719
0.88	High Similarity	NPC473134
0.88	High Similarity	NPC473221
0.879	High Similarity	NPC293801
0.877	High Similarity	NPC476633
0.876	High Similarity	NPC473107
0.875	High Similarity	NPC74821
0.874	High Similarity	NPC474481
0.8739	High Similarity	NPC150624
0.8739	High Similarity	NPC141090
0.8739	High Similarity	NPC54507
0.8739	High Similarity	NPC203113
0.8739	High Similarity	NPC85292
0.8739	High Similarity	NPC229147
0.8729	High Similarity	NPC228287
0.8729	High Similarity	NPC180508
0.872	High Similarity	NPC82299
0.872	High Similarity	NPC283049
0.872	High Similarity	NPC50315
0.872	High Similarity	NPC476006
0.872	High Similarity	NPC230479
0.872	High Similarity	NPC26879
0.871	High Similarity	NPC138248
0.871	High Similarity	NPC159132
0.871	High Similarity	NPC228503
0.8707	High Similarity	NPC106141
0.8699	High Similarity	NPC36016
0.8699	High Similarity	NPC100099
0.8678	High Similarity	NPC184302
0.8672	High Similarity	NPC68205
0.8672	High Similarity	NPC211413
0.8672	High Similarity	NPC244888
0.8672	High Similarity	NPC118683
0.8672	High Similarity	NPC293203
0.8672	High Similarity	NPC164804
0.8667	High Similarity	NPC221549
0.8667	High Similarity	NPC195466
0.8667	High Similarity	NPC50521
0.8667	High Similarity	NPC244816
0.8661	High Similarity	NPC471519
0.8661	High Similarity	NPC472797
0.8661	High Similarity	NPC134360
0.8661	High Similarity	NPC471518
0.8655	High Similarity	NPC53906
0.8655	High Similarity	NPC808
0.8651	High Similarity	NPC149796
0.864	High Similarity	NPC278955
0.864	High Similarity	NPC105718
0.8632	High Similarity	NPC255068
0.8629	High Similarity	NPC38761
0.8629	High Similarity	NPC76465
0.8626	High Similarity	NPC234952
0.8618	High Similarity	NPC52247
0.8618	High Similarity	NPC54972
0.8618	High Similarity	NPC193364
0.8607	High Similarity	NPC282255
0.8605	High Similarity	NPC472798
0.8595	High Similarity	NPC190514
0.8595	High Similarity	NPC131118
0.8594	High Similarity	NPC126836
0.8594	High Similarity	NPC254000
0.8583	High Similarity	NPC211179
0.8583	High Similarity	NPC38664
0.8583	High Similarity	NPC53986
0.8583	High Similarity	NPC215300
0.8583	High Similarity	NPC38604
0.8571	High Similarity	NPC234568
0.8571	High Similarity	NPC276737
0.8571	High Similarity	NPC22610
0.8571	High Similarity	NPC101894
0.856	High Similarity	NPC228972
0.856	High Similarity	NPC197351
0.856	High Similarity	NPC86502
0.856	High Similarity	NPC122792
0.856	High Similarity	NPC106914
0.856	High Similarity	NPC246648
0.856	High Similarity	NPC134195
0.8559	High Similarity	NPC474920
0.8559	High Similarity	NPC280606
0.855	High Similarity	NPC327382
0.855	High Similarity	NPC15109
0.855	High Similarity	NPC11727
0.8547	High Similarity	NPC168657
0.8538	High Similarity	NPC177712
0.8538	High Similarity	NPC229442
0.8538	High Similarity	NPC168059
0.8538	High Similarity	NPC77196
0.8538	High Similarity	NPC36661
0.8538	High Similarity	NPC92805
0.8538	High Similarity	NPC24913
0.8527	High Similarity	NPC282508
0.8527	High Similarity	NPC473309
0.8527	High Similarity	NPC162801
0.8527	High Similarity	NPC15543
0.8527	High Similarity	NPC472590
0.8516	High Similarity	NPC472795
0.8516	High Similarity	NPC472796
0.8516	High Similarity	NPC93962
0.8512	High Similarity	NPC15860
0.8512	High Similarity	NPC219070
0.8512	High Similarity	NPC127894
0.8512	High Similarity	NPC470759
0.8507	High Similarity	NPC71046
0.8504	High Similarity	NPC243688
0.8504	High Similarity	NPC210355
0.8504	High Similarity	NPC53781
0.85	High Similarity	NPC167934
0.8496	Intermediate Similarity	NPC32630
0.8492	Intermediate Similarity	NPC285040
0.8492	Intermediate Similarity	NPC188022
0.8492	Intermediate Similarity	NPC102540
0.8492	Intermediate Similarity	NPC17809
0.8492	Intermediate Similarity	NPC103420
0.8492	Intermediate Similarity	NPC60885
0.8492	Intermediate Similarity	NPC234400
0.8492	Intermediate Similarity	NPC105925
0.8485	Intermediate Similarity	NPC126101
0.848	Intermediate Similarity	NPC474160
0.8475	Intermediate Similarity	NPC90520
0.8475	Intermediate Similarity	NPC296920
0.8473	Intermediate Similarity	NPC223008
0.8473	Intermediate Similarity	NPC296915
0.8473	Intermediate Similarity	NPC225696
0.8473	Intermediate Similarity	NPC198154
0.8473	Intermediate Similarity	NPC97834
0.8473	Intermediate Similarity	NPC115335
0.8468	Intermediate Similarity	NPC187868
0.8462	Intermediate Similarity	NPC13005
0.8455	Intermediate Similarity	NPC258979
0.8455	Intermediate Similarity	NPC8283
0.8455	Intermediate Similarity	NPC3239
0.8455	Intermediate Similarity	NPC93398
0.845	Intermediate Similarity	NPC91291
0.8438	Intermediate Similarity	NPC39064
0.8438	Intermediate Similarity	NPC47283
0.8438	Intermediate Similarity	NPC274717
0.8438	Intermediate Similarity	NPC222572
0.8438	Intermediate Similarity	NPC87224
0.8438	Intermediate Similarity	NPC38017
0.8433	Intermediate Similarity	NPC198038
0.8433	Intermediate Similarity	NPC109240
0.843	Intermediate Similarity	NPC114064
0.8425	Intermediate Similarity	NPC103823
0.8425	Intermediate Similarity	NPC18924
0.8425	Intermediate Similarity	NPC276212
0.8425	Intermediate Similarity	NPC78974
0.8425	Intermediate Similarity	NPC214406
0.8425	Intermediate Similarity	NPC223953
0.8425	Intermediate Similarity	NPC223136
0.8425	Intermediate Similarity	NPC44748
0.8425	Intermediate Similarity	NPC28730
0.8417	Intermediate Similarity	NPC107240
0.8413	Intermediate Similarity	NPC140521
0.8409	Intermediate Similarity	NPC151224
0.84	Intermediate Similarity	NPC194626
0.84	Intermediate Similarity	NPC18128
0.84	Intermediate Similarity	NPC77789
0.8397	Intermediate Similarity	NPC11060
0.8397	Intermediate Similarity	NPC85435
0.8397	Intermediate Similarity	NPC475840
0.8397	Intermediate Similarity	NPC32778
0.839	Intermediate Similarity	NPC94045
0.8385	Intermediate Similarity	NPC150011
0.8385	Intermediate Similarity	NPC164574
0.8385	Intermediate Similarity	NPC129106
0.8385	Intermediate Similarity	NPC207892
0.8385	Intermediate Similarity	NPC300875
0.8385	Intermediate Similarity	NPC129784
0.8385	Intermediate Similarity	NPC118114
0.8385	Intermediate Similarity	NPC236014
0.8385	Intermediate Similarity	NPC228369

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 NPC74137 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	1038
0.2-0.3	1703
0.3-0.4	2757
0.4-0.5	1608
0.5-0.6	936
0.6-0.7	628
0.7-0.8	105
0.8-0.85	5
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.896	High Similarity	NPD4625	Phase 3
0.8934	High Similarity	NPD4749	Approved
0.875	High Similarity	NPD1548	Phase 1
0.8618	High Similarity	NPD1610	Phase 2
0.8618	High Similarity	NPD422	Phase 1
0.8583	High Similarity	NPD4908	Phase 1
0.845	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.845	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8347	Intermediate Similarity	NPD6671	Approved
0.8295	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6099	Approved
0.8148	Intermediate Similarity	NPD6100	Approved
0.814	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6696	Suspended
0.8077	Intermediate Similarity	NPD2861	Phase 2
0.8045	Intermediate Similarity	NPD1613	Approved
0.8045	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD940	Approved
0.8017	Intermediate Similarity	NPD846	Approved
0.8	Intermediate Similarity	NPD4750	Phase 3
0.7955	Intermediate Similarity	NPD3027	Phase 3
0.7914	Intermediate Similarity	NPD3750	Approved
0.7907	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4060	Phase 1
0.7778	Intermediate Similarity	NPD1242	Phase 1
0.7742	Intermediate Similarity	NPD1398	Phase 1
0.7734	Intermediate Similarity	NPD4626	Approved
0.7721	Intermediate Similarity	NPD5124	Phase 1
0.7721	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD7340	Approved
0.7669	Intermediate Similarity	NPD3018	Phase 2
0.766	Intermediate Similarity	NPD3892	Phase 2
0.7623	Intermediate Similarity	NPD2684	Approved
0.7589	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD228	Approved
0.7569	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7447	Phase 1
0.7554	Intermediate Similarity	NPD3748	Approved
0.7541	Intermediate Similarity	NPD290	Approved
0.7519	Intermediate Similarity	NPD5691	Approved
0.7519	Intermediate Similarity	NPD2797	Approved
0.7518	Intermediate Similarity	NPD2238	Phase 2
0.75	Intermediate Similarity	NPD7212	Phase 2
0.75	Intermediate Similarity	NPD2983	Phase 2
0.75	Intermediate Similarity	NPD1511	Approved
0.75	Intermediate Similarity	NPD7213	Phase 3
0.75	Intermediate Similarity	NPD2982	Phase 2
0.7481	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1091	Approved
0.748	Intermediate Similarity	NPD7157	Approved
0.748	Intermediate Similarity	NPD709	Approved
0.7463	Intermediate Similarity	NPD6584	Phase 3
0.7462	Intermediate Similarity	NPD1778	Approved
0.7459	Intermediate Similarity	NPD968	Approved
0.7448	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD8651	Approved
0.7424	Intermediate Similarity	NPD2233	Approved
0.7424	Intermediate Similarity	NPD2981	Phase 2
0.7424	Intermediate Similarity	NPD1608	Approved
0.7424	Intermediate Similarity	NPD2230	Approved
0.7424	Intermediate Similarity	NPD2232	Approved
0.741	Intermediate Similarity	NPD4097	Suspended
0.7405	Intermediate Similarity	NPD3496	Discontinued
0.74	Intermediate Similarity	NPD2801	Approved
0.74	Intermediate Similarity	NPD7819	Suspended
0.7397	Intermediate Similarity	NPD1512	Approved
0.7395	Intermediate Similarity	NPD3020	Approved
0.7391	Intermediate Similarity	NPD1240	Approved
0.7381	Intermediate Similarity	NPD821	Approved
0.7381	Intermediate Similarity	NPD7843	Approved
0.7376	Intermediate Similarity	NPD2796	Approved
0.7368	Intermediate Similarity	NPD5327	Phase 3
0.735	Intermediate Similarity	NPD2933	Approved
0.735	Intermediate Similarity	NPD2934	Approved
0.7348	Intermediate Similarity	NPD3705	Approved
0.7343	Intermediate Similarity	NPD1652	Phase 2
0.7338	Intermediate Similarity	NPD5735	Approved
0.7333	Intermediate Similarity	NPD4624	Approved
0.7324	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD5283	Phase 1
0.7313	Intermediate Similarity	NPD3225	Approved
0.7305	Intermediate Similarity	NPD1510	Phase 2
0.7299	Intermediate Similarity	NPD7095	Approved
0.7297	Intermediate Similarity	NPD1653	Approved
0.7292	Intermediate Similarity	NPD7466	Approved
0.7288	Intermediate Similarity	NPD2859	Approved
0.7288	Intermediate Similarity	NPD844	Approved
0.7288	Intermediate Similarity	NPD2860	Approved
0.7286	Intermediate Similarity	NPD1607	Approved
0.7286	Intermediate Similarity	NPD6353	Approved
0.7286	Intermediate Similarity	NPD2157	Approved
0.7285	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1712	Approved
0.7273	Intermediate Similarity	NPD1549	Phase 2
0.7266	Intermediate Similarity	NPD1558	Phase 1
0.7266	Intermediate Similarity	NPD4140	Approved
0.7252	Intermediate Similarity	NPD3445	Approved
0.7252	Intermediate Similarity	NPD3443	Approved
0.7252	Intermediate Similarity	NPD3444	Approved
0.7246	Intermediate Similarity	NPD1296	Phase 2
0.7246	Intermediate Similarity	NPD3268	Approved
0.7244	Intermediate Similarity	NPD5535	Approved
0.7241	Intermediate Similarity	NPD2677	Approved
0.7239	Intermediate Similarity	NPD6582	Phase 2
0.7239	Intermediate Similarity	NPD6583	Phase 3
0.7227	Intermediate Similarity	NPD288	Approved
0.7219	Intermediate Similarity	NPD1934	Approved
0.7218	Intermediate Similarity	NPD1611	Approved
0.7211	Intermediate Similarity	NPD2533	Approved
0.7211	Intermediate Similarity	NPD2532	Approved
0.7211	Intermediate Similarity	NPD2534	Approved
0.7206	Intermediate Similarity	NPD3690	Phase 2
0.7206	Intermediate Similarity	NPD3691	Phase 2
0.7203	Intermediate Similarity	NPD5762	Approved
0.7203	Intermediate Similarity	NPD5763	Approved
0.7203	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2668	Approved
0.7197	Intermediate Similarity	NPD17	Approved
0.7197	Intermediate Similarity	NPD2667	Approved
0.719	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3882	Suspended
0.7183	Intermediate Similarity	NPD7033	Discontinued
0.7164	Intermediate Similarity	NPD1840	Phase 2
0.7164	Intermediate Similarity	NPD2231	Phase 2
0.7164	Intermediate Similarity	NPD2235	Phase 2
0.7162	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3022	Approved
0.7143	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD3021	Approved
0.7133	Intermediate Similarity	NPD1551	Phase 2
0.7124	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1651	Approved
0.7115	Intermediate Similarity	NPD7199	Phase 2
0.7115	Intermediate Similarity	NPD6959	Discontinued
0.7113	Intermediate Similarity	NPD2200	Suspended
0.7111	Intermediate Similarity	NPD1669	Approved
0.7109	Intermediate Similarity	NPD7635	Approved
0.7103	Intermediate Similarity	NPD2800	Approved
0.7097	Intermediate Similarity	NPD9697	Approved
0.7083	Intermediate Similarity	NPD3540	Phase 1
0.7078	Intermediate Similarity	NPD7768	Phase 2
0.707	Intermediate Similarity	NPD7229	Phase 3
0.7059	Intermediate Similarity	NPD1283	Approved
0.7055	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7037	Approved
0.7027	Intermediate Similarity	NPD6799	Approved
0.7025	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3620	Phase 2
0.702	Intermediate Similarity	NPD4005	Discontinued
0.7014	Intermediate Similarity	NPD2935	Discontinued
0.7014	Intermediate Similarity	NPD3539	Phase 1
0.7014	Intermediate Similarity	NPD4477	Approved
0.7014	Intermediate Similarity	NPD4476	Approved
0.7013	Intermediate Similarity	NPD2560	Approved
0.7013	Intermediate Similarity	NPD2563	Approved
0.7013	Intermediate Similarity	NPD3817	Phase 2
0.7013	Intermediate Similarity	NPD4288	Approved
0.7008	Intermediate Similarity	NPD5451	Approved
0.7	Intermediate Similarity	NPD1809	Phase 2
0.6993	Remote Similarity	NPD37	Approved
0.6992	Remote Similarity	NPD5585	Approved
0.6987	Remote Similarity	NPD6234	Discontinued
0.6986	Remote Similarity	NPD6674	Discontinued
0.6985	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2342	Discontinued
0.698	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD845	Approved
0.6974	Remote Similarity	NPD4675	Approved
0.6974	Remote Similarity	NPD4380	Phase 2
0.6974	Remote Similarity	NPD4678	Approved
0.6972	Remote Similarity	NPD6355	Discontinued
0.697	Remote Similarity	NPD7644	Approved
0.6968	Remote Similarity	NPD4967	Phase 2
0.6968	Remote Similarity	NPD4966	Approved
0.6968	Remote Similarity	NPD4965	Approved
0.6968	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD1535	Discovery
0.6962	Remote Similarity	NPD6232	Discontinued
0.6959	Remote Similarity	NPD6667	Approved
0.6959	Remote Similarity	NPD6666	Approved
0.6957	Remote Similarity	NPD5844	Phase 1
0.695	Remote Similarity	NPD8032	Phase 2
0.6948	Remote Similarity	NPD1465	Phase 2
0.6947	Remote Similarity	NPD2557	Approved
0.6944	Remote Similarity	NPD2155	Approved
0.6944	Remote Similarity	NPD4308	Phase 3
0.6944	Remote Similarity	NPD2156	Approved
0.6944	Remote Similarity	NPD2154	Approved
0.694	Remote Similarity	NPD6516	Phase 2
0.694	Remote Similarity	NPD5846	Approved
0.694	Remote Similarity	NPD4059	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