NPASS Compound

Structure

CID85895 OpenBabel06191715422D 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 -3.4641 -0.0000 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 -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 -1.7321 2.0000 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 -1.7321 3.0000 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 19 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 20 1 0 0 0 0 15 18 1 0 0 0 0 15 21 2 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 20 23 1 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:	6.806
LogD:	5.257
LogS:	-6.264
# 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:	3.569
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:	-4.827
MDCK Permeability:	2.3401444195769727e-05
Pgp-inhibitor:	0.961
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.952
30% Bioavailability (F30%):	0.155

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.143
Plasma Protein Binding (PPB):	100.30554962158203%
Volume Distribution (VD):	3.586
Pgp-substrate:	2.071600914001465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.934
CYP1A2-substrate:	0.358
CYP2C19-inhibitor:	0.781
CYP2C19-substrate:	0.786
CYP2C9-inhibitor:	0.715
CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.959
CYP2D6-substrate:	0.551
CYP3A4-inhibitor:	0.908
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	8.227
Half-life (T1/2):	0.17

ADMET: Toxicity

hERG Blockers:	0.354
Human Hepatotoxicity (H-HT):	0.945
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.625
Skin Sensitization:	0.949
Carcinogencity:	0.088
Eye Corrosion:	0.017
Eye Irritation:	0.883
Respiratory Toxicity:	0.571

Download Data

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

Natural Product: NPC85895

Natural Product ID:	NPC85895
*Common Name:**	Confluentin
IUPAC Name:	(2R)-2-[(3E)-4,8-dimethylnona-3,7-dienyl]-2,7-dimethylchromen-5-ol
Synonyms:	Confluentin
Standard InCHIKey:	WQOSNKWCIQZRGH-IHSQGBLNSA-N
Standard InCHI:	InChI=1S/C22H30O2/c1-16(2)8-6-9-17(3)10-7-12-22(5)13-11-19-20(23)14-18(4)15-21(19)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(cc2O)C)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449069
PubChem CID:	10381750
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
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1007/BF02329610]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270561]
NPO10941	Albatrellus ovinus	Species	Albatrellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23305465]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10941	Albatrellus ovinus	Species	Albatrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	23010.0	nM	PMID[539150]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	18480.0	nM	PMID[539150]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	15050.0	nM	PMID[539150]
NPT2	Others	Unspecified		IC50	=	205.0	uL	PMID[539149]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	17080.0	nM	PMID[539150]

☑ 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 NPC85895 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	362
0.1-0.2	1834
0.2-0.3	5661
0.3-0.4	13658
0.4-0.5	3765
0.5-0.6	5684
0.6-0.7	8554
0.7-0.8	2762
0.8-0.85	339
0.85-0.9	60
0.9-0.95	13
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC137294
0.9823	High Similarity	NPC218753
0.9737	High Similarity	NPC212965
0.9652	High Similarity	NPC120638
0.9487	High Similarity	NPC270030
0.9407	High Similarity	NPC476254
0.9407	High Similarity	NPC131397
0.9316	High Similarity	NPC74137
0.925	High Similarity	NPC46978
0.9237	High Similarity	NPC96940
0.9138	High Similarity	NPC184302
0.9052	High Similarity	NPC190514
0.9024	High Similarity	NPC474481
0.9008	High Similarity	NPC476006
0.8966	High Similarity	NPC33270
0.8966	High Similarity	NPC69261
0.8952	High Similarity	NPC82503
0.8943	High Similarity	NPC16577
0.8943	High Similarity	NPC96719
0.8943	High Similarity	NPC222108
0.8938	High Similarity	NPC255068
0.8879	High Similarity	NPC150624
0.8862	High Similarity	NPC38604
0.8862	High Similarity	NPC211179
0.886	High Similarity	NPC474920
0.8833	High Similarity	NPC77789
0.8833	High Similarity	NPC18128
0.881	High Similarity	NPC36661
0.88	High Similarity	NPC472590
0.8793	High Similarity	NPC808
0.8793	High Similarity	NPC53906
0.879	High Similarity	NPC472797
0.879	High Similarity	NPC472795
0.879	High Similarity	NPC472796
0.873	High Similarity	NPC469611
0.8718	High Similarity	NPC203113
0.8707	High Similarity	NPC228287
0.8707	High Similarity	NPC180508
0.8707	High Similarity	NPC276737
0.8707	High Similarity	NPC22610
0.8689	High Similarity	NPC159132
0.8684	High Similarity	NPC168657
0.8684	High Similarity	NPC106141
0.8684	High Similarity	NPC94045
0.8667	High Similarity	NPC102639
0.8661	High Similarity	NPC164576
0.8661	High Similarity	NPC469610
0.8655	High Similarity	NPC471449
0.8655	High Similarity	NPC295259
0.8651	High Similarity	NPC160623
0.8651	High Similarity	NPC8899
0.8644	High Similarity	NPC221549
0.8644	High Similarity	NPC127894
0.8644	High Similarity	NPC244816
0.8644	High Similarity	NPC474933
0.8644	High Similarity	NPC219070
0.8644	High Similarity	NPC470759
0.8644	High Similarity	NPC50521
0.8644	High Similarity	NPC15860
0.8632	High Similarity	NPC185541
0.8632	High Similarity	NPC464
0.8632	High Similarity	NPC473718
0.8618	High Similarity	NPC105031
0.8595	High Similarity	NPC476633
0.8595	High Similarity	NPC75713
0.8583	High Similarity	NPC472798
0.8571	High Similarity	NPC229231
0.8571	High Similarity	NPC74821
0.8559	High Similarity	NPC54507
0.8559	High Similarity	NPC85292
0.8559	High Similarity	NPC141090
0.8559	High Similarity	NPC114064
0.8559	High Similarity	NPC229147
0.8548	High Similarity	NPC244364
0.8538	High Similarity	NPC35550
0.8538	High Similarity	NPC476171
0.8537	High Similarity	NPC140521
0.8534	High Similarity	NPC280606
0.8525	High Similarity	NPC36016
0.8525	High Similarity	NPC100099
0.8516	High Similarity	NPC269528
0.8516	High Similarity	NPC94236
0.8516	High Similarity	NPC37196
0.8492	Intermediate Similarity	NPC134360
0.848	Intermediate Similarity	NPC236760
0.848	Intermediate Similarity	NPC473221
0.848	Intermediate Similarity	NPC149796
0.848	Intermediate Similarity	NPC473134
0.8475	Intermediate Similarity	NPC167934
0.8468	Intermediate Similarity	NPC249836
0.8468	Intermediate Similarity	NPC293801
0.8462	Intermediate Similarity	NPC126101
0.8455	Intermediate Similarity	NPC95168
0.8455	Intermediate Similarity	NPC38761
0.8455	Intermediate Similarity	NPC261992
0.8455	Intermediate Similarity	NPC76465
0.8448	Intermediate Similarity	NPC296920
0.8448	Intermediate Similarity	NPC90520
0.8443	Intermediate Similarity	NPC52247
0.8443	Intermediate Similarity	NPC54972
0.8438	Intermediate Similarity	NPC161203
0.8435	Intermediate Similarity	NPC19808
0.8435	Intermediate Similarity	NPC33728
0.8421	Intermediate Similarity	NPC204901
0.8421	Intermediate Similarity	NPC158253
0.8421	Intermediate Similarity	NPC35543
0.8421	Intermediate Similarity	NPC232523
0.8417	Intermediate Similarity	NPC131118
0.8407	Intermediate Similarity	NPC37802
0.84	Intermediate Similarity	NPC170485
0.84	Intermediate Similarity	NPC50315
0.84	Intermediate Similarity	NPC283049
0.84	Intermediate Similarity	NPC26879
0.84	Intermediate Similarity	NPC230479
0.84	Intermediate Similarity	NPC82299
0.8387	Intermediate Similarity	NPC228972
0.8387	Intermediate Similarity	NPC78446
0.8387	Intermediate Similarity	NPC197351
0.8387	Intermediate Similarity	NPC122792
0.8387	Intermediate Similarity	NPC86502
0.8387	Intermediate Similarity	NPC134195
0.8387	Intermediate Similarity	NPC106914
0.8387	Intermediate Similarity	NPC246648
0.8385	Intermediate Similarity	NPC327382
0.8385	Intermediate Similarity	NPC201357
0.8385	Intermediate Similarity	NPC281521
0.8385	Intermediate Similarity	NPC255147
0.8374	Intermediate Similarity	NPC474864
0.8374	Intermediate Similarity	NPC188997
0.8374	Intermediate Similarity	NPC194626
0.8372	Intermediate Similarity	NPC168059
0.8372	Intermediate Similarity	NPC229442
0.8362	Intermediate Similarity	NPC2682
0.8359	Intermediate Similarity	NPC118683
0.8359	Intermediate Similarity	NPC293203
0.8359	Intermediate Similarity	NPC211413
0.8359	Intermediate Similarity	NPC244888
0.8359	Intermediate Similarity	NPC164804
0.8359	Intermediate Similarity	NPC68205
0.8359	Intermediate Similarity	NPC469907
0.8348	Intermediate Similarity	NPC174981
0.8348	Intermediate Similarity	NPC245115
0.8347	Intermediate Similarity	NPC51341
0.8333	Intermediate Similarity	NPC201662
0.8333	Intermediate Similarity	NPC473653
0.8333	Intermediate Similarity	NPC195466
0.8333	Intermediate Similarity	NPC99836
0.8333	Intermediate Similarity	NPC216836
0.8333	Intermediate Similarity	NPC12640
0.8333	Intermediate Similarity	NPC210355
0.8333	Intermediate Similarity	NPC243688
0.8321	Intermediate Similarity	NPC327735
0.8321	Intermediate Similarity	NPC472800
0.8321	Intermediate Similarity	NPC476698
0.832	Intermediate Similarity	NPC113495
0.832	Intermediate Similarity	NPC299584
0.832	Intermediate Similarity	NPC82483
0.832	Intermediate Similarity	NPC285040
0.832	Intermediate Similarity	NPC188022
0.832	Intermediate Similarity	NPC102540
0.832	Intermediate Similarity	NPC234400
0.832	Intermediate Similarity	NPC105925
0.832	Intermediate Similarity	NPC17809
0.832	Intermediate Similarity	NPC60885
0.832	Intermediate Similarity	NPC265483
0.832	Intermediate Similarity	NPC103420
0.8319	Intermediate Similarity	NPC244513
0.8319	Intermediate Similarity	NPC218879
0.8319	Intermediate Similarity	NPC227458
0.8306	Intermediate Similarity	NPC474160
0.8293	Intermediate Similarity	NPC193364
0.8293	Intermediate Similarity	NPC187868
0.8291	Intermediate Similarity	NPC224527
0.8281	Intermediate Similarity	NPC91291
0.8281	Intermediate Similarity	NPC220935
0.8281	Intermediate Similarity	NPC214860
0.8279	Intermediate Similarity	NPC93398
0.8279	Intermediate Similarity	NPC247553
0.8279	Intermediate Similarity	NPC258979
0.8279	Intermediate Similarity	NPC8283
0.8276	Intermediate Similarity	NPC299568
0.8276	Intermediate Similarity	NPC82016
0.8276	Intermediate Similarity	NPC186385
0.8268	Intermediate Similarity	NPC38664
0.8268	Intermediate Similarity	NPC53986
0.8268	Intermediate Similarity	NPC87224
0.8268	Intermediate Similarity	NPC63179
0.8268	Intermediate Similarity	NPC215300
0.8268	Intermediate Similarity	NPC222572
0.8268	Intermediate Similarity	NPC274717
0.8264	Intermediate Similarity	NPC283616
0.8258	Intermediate Similarity	NPC134260
0.8254	Intermediate Similarity	NPC276212
0.8254	Intermediate Similarity	NPC18924
0.8254	Intermediate Similarity	NPC44748
0.8254	Intermediate Similarity	NPC214406
0.8254	Intermediate Similarity	NPC28730
0.8254	Intermediate Similarity	NPC78974
0.8254	Intermediate Similarity	NPC223136
0.8254	Intermediate Similarity	NPC103823

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 NPC85895 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	349
0.1-0.2	1040
0.2-0.3	1753
0.3-0.4	2798
0.4-0.5	1573
0.5-0.6	1022
0.6-0.7	544
0.7-0.8	57
0.8-0.85	10
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9237	High Similarity	NPD4749	Approved
0.8943	High Similarity	NPD4625	Phase 3
0.872	High Similarity	NPD6410	Clinical (unspecified phase)
0.8571	High Similarity	NPD1548	Phase 1
0.8475	Intermediate Similarity	NPD6671	Approved
0.8443	Intermediate Similarity	NPD422	Phase 1
0.8293	Intermediate Similarity	NPD1610	Phase 2
0.8276	Intermediate Similarity	NPD4750	Phase 3
0.8268	Intermediate Similarity	NPD4908	Phase 1
0.8258	Intermediate Similarity	NPD6099	Approved
0.8258	Intermediate Similarity	NPD6100	Approved
0.8254	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD6696	Suspended
0.8047	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD1778	Approved
0.7879	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1613	Approved
0.7826	Intermediate Similarity	NPD940	Approved
0.7826	Intermediate Similarity	NPD846	Approved
0.7797	Intermediate Similarity	NPD290	Approved
0.7786	Intermediate Similarity	NPD3027	Phase 3
0.7769	Intermediate Similarity	NPD2861	Phase 2
0.7739	Intermediate Similarity	NPD1242	Phase 1
0.7727	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD1091	Approved
0.7712	Intermediate Similarity	NPD968	Approved
0.7705	Intermediate Similarity	NPD1398	Phase 1
0.7699	Intermediate Similarity	NPD844	Approved
0.7661	Intermediate Similarity	NPD7340	Approved
0.7634	Intermediate Similarity	NPD3018	Phase 2
0.7591	Intermediate Similarity	NPD1551	Phase 2
0.7556	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD5124	Phase 1
0.7538	Intermediate Similarity	NPD3225	Approved
0.75	Intermediate Similarity	NPD3496	Discontinued
0.7481	Intermediate Similarity	NPD2797	Approved
0.7478	Intermediate Similarity	NPD288	Approved
0.7462	Intermediate Similarity	NPD2983	Phase 2
0.7462	Intermediate Similarity	NPD2982	Phase 2
0.7438	Intermediate Similarity	NPD2684	Approved
0.7422	Intermediate Similarity	NPD4626	Approved
0.7413	Intermediate Similarity	NPD7447	Phase 1
0.7413	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD228	Approved
0.7385	Intermediate Similarity	NPD2981	Phase 2
0.7385	Intermediate Similarity	NPD1608	Approved
0.7376	Intermediate Similarity	NPD3892	Phase 2
0.7376	Intermediate Similarity	NPD3750	Approved
0.7372	Intermediate Similarity	NPD1607	Approved
0.7357	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1511	Approved
0.7343	Intermediate Similarity	NPD7213	Phase 3
0.7343	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD7212	Phase 2
0.7333	Intermediate Similarity	NPD9697	Approved
0.7328	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6584	Phase 3
0.7292	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD4308	Phase 3
0.7266	Intermediate Similarity	NPD7033	Discontinued
0.726	Intermediate Similarity	NPD1653	Approved
0.7252	Intermediate Similarity	NPD2233	Approved
0.7252	Intermediate Similarity	NPD2230	Approved
0.7252	Intermediate Similarity	NPD2235	Phase 2
0.7252	Intermediate Similarity	NPD2231	Phase 2
0.7252	Intermediate Similarity	NPD2232	Approved
0.7248	Intermediate Similarity	NPD2801	Approved
0.7241	Intermediate Similarity	NPD1512	Approved
0.7226	Intermediate Similarity	NPD2238	Phase 2
0.7226	Intermediate Similarity	NPD4060	Phase 1
0.7226	Intermediate Similarity	NPD1240	Approved
0.7214	Intermediate Similarity	NPD2796	Approved
0.7209	Intermediate Similarity	NPD5691	Approved
0.7206	Intermediate Similarity	NPD3268	Approved
0.7206	Intermediate Similarity	NPD411	Approved
0.72	Intermediate Similarity	NPD821	Approved
0.72	Intermediate Similarity	NPD7843	Approved
0.7183	Intermediate Similarity	NPD1652	Phase 2
0.7176	Intermediate Similarity	NPD1611	Approved
0.7172	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD709	Approved
0.7165	Intermediate Similarity	NPD7157	Approved
0.7163	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD2934	Approved
0.7155	Intermediate Similarity	NPD2933	Approved
0.7154	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD1510	Phase 2
0.7143	Intermediate Similarity	NPD8651	Approved
0.7143	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD4097	Suspended
0.7121	Intermediate Similarity	NPD9717	Approved
0.7113	Intermediate Similarity	NPD1549	Phase 2
0.7101	Intermediate Similarity	NPD1558	Phase 1
0.7094	Intermediate Similarity	NPD2859	Approved
0.7094	Intermediate Similarity	NPD2860	Approved
0.709	Intermediate Similarity	NPD1203	Approved
0.708	Intermediate Similarity	NPD1296	Phase 2
0.7077	Intermediate Similarity	NPD5585	Approved
0.7071	Intermediate Similarity	NPD2200	Suspended
0.7068	Intermediate Similarity	NPD6583	Phase 3
0.7068	Intermediate Similarity	NPD6582	Phase 2
0.7067	Intermediate Similarity	NPD1934	Approved
0.7063	Intermediate Similarity	NPD7635	Approved
0.7063	Intermediate Similarity	NPD5535	Approved
0.7059	Intermediate Similarity	NPD3020	Approved
0.7042	Intermediate Similarity	NPD3540	Phase 1
0.7042	Intermediate Similarity	NPD5763	Approved
0.7042	Intermediate Similarity	NPD5762	Approved
0.7039	Intermediate Similarity	NPD3882	Suspended
0.7037	Intermediate Similarity	NPD3690	Phase 2
0.7037	Intermediate Similarity	NPD3691	Phase 2
0.7031	Intermediate Similarity	NPD2557	Approved
0.7023	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3748	Approved
0.7014	Intermediate Similarity	NPD7466	Approved
0.7008	Intermediate Similarity	NPD5283	Phase 1
0.7007	Intermediate Similarity	NPD7095	Approved
0.6985	Remote Similarity	NPD1712	Approved
0.6978	Remote Similarity	NPD4307	Phase 2
0.6972	Remote Similarity	NPD3539	Phase 1
0.6947	Remote Similarity	NPD3444	Approved
0.6947	Remote Similarity	NPD3443	Approved
0.6947	Remote Similarity	NPD3445	Approved
0.694	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5327	Phase 3
0.6939	Remote Similarity	NPD2532	Approved
0.6939	Remote Similarity	NPD2534	Approved
0.6939	Remote Similarity	NPD2533	Approved
0.6935	Remote Similarity	NPD2342	Discontinued
0.6934	Remote Similarity	NPD596	Approved
0.6934	Remote Similarity	NPD600	Approved
0.6933	Remote Similarity	NPD4675	Approved
0.6933	Remote Similarity	NPD4678	Approved
0.6929	Remote Similarity	NPD5735	Approved
0.6929	Remote Similarity	NPD447	Suspended
0.6923	Remote Similarity	NPD7644	Approved
0.6923	Remote Similarity	NPD845	Approved
0.6912	Remote Similarity	NPD4624	Approved
0.6908	Remote Similarity	NPD7819	Suspended
0.6894	Remote Similarity	NPD2667	Approved
0.6894	Remote Similarity	NPD2668	Approved
0.6894	Remote Similarity	NPD2107	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6353	Approved
0.6871	Remote Similarity	NPD6799	Approved
0.687	Remote Similarity	NPD9295	Approved
0.687	Remote Similarity	NPD1182	Approved
0.687	Remote Similarity	NPD2486	Discontinued
0.6864	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5402	Approved
0.6863	Remote Similarity	NPD3817	Phase 2
0.6863	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD2237	Approved
0.6859	Remote Similarity	NPD6959	Discontinued
0.6857	Remote Similarity	NPD4140	Approved
0.6855	Remote Similarity	NPD3134	Approved
0.6853	Remote Similarity	NPD2935	Discontinued
0.6849	Remote Similarity	NPD2677	Approved
0.6847	Remote Similarity	NPD9089	Approved
0.6846	Remote Similarity	NPD5403	Approved
0.6838	Remote Similarity	NPD3267	Approved
0.6838	Remote Similarity	NPD3266	Approved
0.6835	Remote Similarity	NPD1048	Approved
0.6828	Remote Similarity	NPD2800	Approved
0.6825	Remote Similarity	NPD3022	Approved
0.6825	Remote Similarity	NPD3021	Approved
0.6825	Remote Similarity	NPD5451	Approved
0.6821	Remote Similarity	NPD4380	Phase 2
0.6821	Remote Similarity	NPD6599	Discontinued
0.6818	Remote Similarity	NPD1357	Approved
0.6818	Remote Similarity	NPD7768	Phase 2
0.6818	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3049	Approved
0.6818	Remote Similarity	NPD1651	Approved
0.6815	Remote Similarity	NPD4359	Approved
0.6814	Remote Similarity	NPD111	Approved
0.6806	Remote Similarity	NPD6004	Phase 3
0.6806	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6002	Phase 3
0.6806	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6005	Phase 3
0.6803	Remote Similarity	NPD6815	Approved
0.6795	Remote Similarity	NPD6746	Phase 2
0.6791	Remote Similarity	NPD1535	Discovery
0.6791	Remote Similarity	NPD3705	Approved
0.6788	Remote Similarity	NPD558	Phase 2
0.6786	Remote Similarity	NPD840	Approved
0.6786	Remote Similarity	NPD839	Approved
0.6781	Remote Similarity	NPD4628	Phase 3
0.6776	Remote Similarity	NPD7411	Suspended
0.6776	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4381	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