NPASS Compound

Structure

CID212965 OpenBabel06191716002D 25 26 0 0 1 0 0 0 0 0999 V2000 -3.9533 1.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9545 -2.7600 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 -5.1780 0.1378 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 -4.2814 -3.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2121 0.3966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9885 -2.5012 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 -4.5403 -4.1742 0.0000 O 0 0 0 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 17 1 0 0 0 0 3 18 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 11 1 0 0 0 0 7 16 1 0 0 0 0 8 17 2 0 0 0 0 9 16 2 0 0 0 0 10 12 2 0 0 0 0 10 19 1 0 0 0 0 11 22 1 0 0 0 0 12 22 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 14 21 2 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 22 4 1 6 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.22
Volume:	382.507
LogP:	5.06
LogD:	4.31
LogS:	-4.751
# Rotatable Bonds:	7
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.66
Synthetic Accessibility Score:	3.693
Fsp3:	0.455
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:	-4.738
MDCK Permeability:	2.6382511350675486e-05
Pgp-inhibitor:	0.945
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.051
20% Bioavailability (F20%):	0.427
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.161
Plasma Protein Binding (PPB):	99.14641571044922%
Volume Distribution (VD):	0.305
Pgp-substrate:	0.6209306716918945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.816
CYP1A2-substrate:	0.498
CYP2C19-inhibitor:	0.397
CYP2C19-substrate:	0.738
CYP2C9-inhibitor:	0.393
CYP2C9-substrate:	0.86
CYP2D6-inhibitor:	0.955
CYP2D6-substrate:	0.55
CYP3A4-inhibitor:	0.912
CYP3A4-substrate:	0.244

ADMET: Excretion

Clearance (CL):	6.426
Half-life (T1/2):	0.651

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.794
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.959
Carcinogencity:	0.041
Eye Corrosion:	0.027
Eye Irritation:	0.895
Respiratory Toxicity:	0.734

Download Data

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

Natural Product: NPC212965

Natural Product ID:	NPC212965
*Common Name:**	Daurichromene D
IUPAC Name:	(2R)-2-[(3E,7E)-9-hydroxy-4,8-dimethylnona-3,7-dienyl]-2,7-dimethylchromen-5-ol
Synonyms:	Daurichromene D
Standard InCHIKey:	MYAKCCHNPIRCLY-PSMGVCQDSA-N
Standard InCHI:	InChI=1S/C22H30O3/c1-16(7-5-8-17(2)15-23)9-6-11-22(4)12-10-19-20(24)13-18(3)14-21(19)25-22/h8-10,12-14,23-24H,5-7,11,15H2,1-4H3/b16-9+,17-8+/t22-/m1/s1
SMILES:	OC/C(=C/CC/C(=C/CC[C@]1(C)C=Cc2c(O1)cc(cc2O)C)/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487803
PubChem CID:	10427504
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]
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]
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]

☑ 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	=	1.3	uL	PMID[489563]

☑ 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 NPC212965 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	335
0.1-0.2	1568
0.2-0.3	4964
0.3-0.4	13516
0.4-0.5	4633
0.5-0.6	5104
0.6-0.7	8990
0.7-0.8	3075
0.8-0.85	440
0.85-0.9	53
0.9-0.95	12
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9913	High Similarity	NPC120638
0.9737	High Similarity	NPC137294
0.9737	High Similarity	NPC85895
0.9661	High Similarity	NPC476254
0.9661	High Similarity	NPC131397
0.9569	High Similarity	NPC218753
0.9412	High Similarity	NPC270030
0.9106	High Similarity	NPC38604
0.9106	High Similarity	NPC211179
0.9083	High Similarity	NPC77789
0.9083	High Similarity	NPC18128
0.9083	High Similarity	NPC74137
0.9068	High Similarity	NPC184302
0.9032	High Similarity	NPC472795
0.9032	High Similarity	NPC472796
0.9032	High Similarity	NPC472797
0.9024	High Similarity	NPC46978
0.9008	High Similarity	NPC96940
0.8983	High Similarity	NPC190514
0.8898	High Similarity	NPC69261
0.8898	High Similarity	NPC33270
0.8889	High Similarity	NPC472590
0.8889	High Similarity	NPC82503
0.8814	High Similarity	NPC150624
0.881	High Similarity	NPC474481
0.879	High Similarity	NPC476006
0.875	High Similarity	NPC295259
0.875	High Similarity	NPC36661
0.873	High Similarity	NPC222108
0.873	High Similarity	NPC16577
0.873	High Similarity	NPC96719
0.8729	High Similarity	NPC53906
0.8729	High Similarity	NPC808
0.8707	High Similarity	NPC255068
0.8699	High Similarity	NPC261992
0.8672	High Similarity	NPC472798
0.8667	High Similarity	NPC74821
0.8655	High Similarity	NPC203113
0.8644	High Similarity	NPC276737
0.8644	High Similarity	NPC180508
0.8644	High Similarity	NPC22610
0.8644	High Similarity	NPC228287
0.8632	High Similarity	NPC474920
0.8621	High Similarity	NPC106141
0.8621	High Similarity	NPC168657
0.8621	High Similarity	NPC94045
0.8618	High Similarity	NPC36016
0.8618	High Similarity	NPC188997
0.8618	High Similarity	NPC100099
0.8607	High Similarity	NPC102639
0.8605	High Similarity	NPC469610
0.8596	High Similarity	NPC164576
0.8583	High Similarity	NPC221549
0.8583	High Similarity	NPC134360
0.8583	High Similarity	NPC474933
0.8583	High Similarity	NPC127894
0.8583	High Similarity	NPC244816
0.8583	High Similarity	NPC15860
0.8583	High Similarity	NPC470759
0.8583	High Similarity	NPC219070
0.8583	High Similarity	NPC50521
0.8571	High Similarity	NPC149796
0.8571	High Similarity	NPC185541
0.8571	High Similarity	NPC464
0.856	High Similarity	NPC293801
0.856	High Similarity	NPC105031
0.855	High Similarity	NPC476698
0.855	High Similarity	NPC472800
0.855	High Similarity	NPC327735
0.855	High Similarity	NPC126101
0.8548	High Similarity	NPC76465
0.8548	High Similarity	NPC38761
0.8548	High Similarity	NPC474160
0.8537	High Similarity	NPC75713
0.8537	High Similarity	NPC54972
0.8537	High Similarity	NPC476633
0.8527	High Similarity	NPC469611
0.8516	High Similarity	NPC229231
0.8512	High Similarity	NPC283616
0.8504	High Similarity	NPC274717
0.85	High Similarity	NPC229147
0.85	High Similarity	NPC290470
0.85	High Similarity	NPC154256
0.85	High Similarity	NPC114064
0.85	High Similarity	NPC85292
0.85	High Similarity	NPC54507
0.85	High Similarity	NPC141090
0.8492	Intermediate Similarity	NPC244364
0.8492	Intermediate Similarity	NPC230479
0.8492	Intermediate Similarity	NPC283049
0.8492	Intermediate Similarity	NPC50315
0.8492	Intermediate Similarity	NPC276212
0.8492	Intermediate Similarity	NPC26879
0.8487	Intermediate Similarity	NPC161696
0.8485	Intermediate Similarity	NPC134260
0.848	Intermediate Similarity	NPC134195
0.848	Intermediate Similarity	NPC159132
0.848	Intermediate Similarity	NPC246648
0.848	Intermediate Similarity	NPC197351
0.848	Intermediate Similarity	NPC86502
0.848	Intermediate Similarity	NPC106914
0.8475	Intermediate Similarity	NPC280606
0.8462	Intermediate Similarity	NPC37196
0.8462	Intermediate Similarity	NPC94236
0.8462	Intermediate Similarity	NPC229442
0.8462	Intermediate Similarity	NPC168059
0.8462	Intermediate Similarity	NPC269528
0.8462	Intermediate Similarity	NPC475840
0.8455	Intermediate Similarity	NPC96423
0.8455	Intermediate Similarity	NPC199023
0.845	Intermediate Similarity	NPC118683
0.845	Intermediate Similarity	NPC160623
0.845	Intermediate Similarity	NPC293203
0.845	Intermediate Similarity	NPC244888
0.845	Intermediate Similarity	NPC8899
0.845	Intermediate Similarity	NPC164804
0.845	Intermediate Similarity	NPC211413
0.845	Intermediate Similarity	NPC68205
0.8443	Intermediate Similarity	NPC471449
0.8435	Intermediate Similarity	NPC473653
0.8425	Intermediate Similarity	NPC473221
0.8425	Intermediate Similarity	NPC224774
0.8425	Intermediate Similarity	NPC121740
0.8425	Intermediate Similarity	NPC258567
0.8425	Intermediate Similarity	NPC236760
0.8417	Intermediate Similarity	NPC301321
0.8417	Intermediate Similarity	NPC473718
0.8417	Intermediate Similarity	NPC167934
0.8413	Intermediate Similarity	NPC102540
0.8413	Intermediate Similarity	NPC103420
0.8413	Intermediate Similarity	NPC17809
0.8413	Intermediate Similarity	NPC285040
0.8413	Intermediate Similarity	NPC188022
0.84	Intermediate Similarity	NPC95168
0.839	Intermediate Similarity	NPC90520
0.839	Intermediate Similarity	NPC296920
0.8387	Intermediate Similarity	NPC193364
0.8385	Intermediate Similarity	NPC161203
0.8374	Intermediate Similarity	NPC258979
0.8374	Intermediate Similarity	NPC93398
0.8374	Intermediate Similarity	NPC8283
0.8372	Intermediate Similarity	NPC91291
0.8372	Intermediate Similarity	NPC220935
0.8372	Intermediate Similarity	NPC472338
0.8362	Intermediate Similarity	NPC35543
0.8361	Intermediate Similarity	NPC131118
0.8359	Intermediate Similarity	NPC222572
0.8359	Intermediate Similarity	NPC53986
0.8359	Intermediate Similarity	NPC469453
0.8359	Intermediate Similarity	NPC38664
0.8359	Intermediate Similarity	NPC87224
0.8346	Intermediate Similarity	NPC82299
0.8346	Intermediate Similarity	NPC476171
0.8346	Intermediate Similarity	NPC35550
0.8346	Intermediate Similarity	NPC170485
0.8333	Intermediate Similarity	NPC164787
0.8333	Intermediate Similarity	NPC472337
0.8333	Intermediate Similarity	NPC201357
0.8333	Intermediate Similarity	NPC140521
0.8333	Intermediate Similarity	NPC255147
0.8333	Intermediate Similarity	NPC281521
0.8333	Intermediate Similarity	NPC151224
0.8333	Intermediate Similarity	NPC327382
0.8333	Intermediate Similarity	NPC61946
0.8321	Intermediate Similarity	NPC77196
0.8321	Intermediate Similarity	NPC11060
0.8321	Intermediate Similarity	NPC92805
0.832	Intermediate Similarity	NPC474864
0.832	Intermediate Similarity	NPC194626
0.832	Intermediate Similarity	NPC57199
0.8319	Intermediate Similarity	NPC228452
0.8308	Intermediate Similarity	NPC103799
0.8308	Intermediate Similarity	NPC472597
0.8308	Intermediate Similarity	NPC162801
0.8306	Intermediate Similarity	NPC473875
0.8305	Intermediate Similarity	NPC2682
0.8296	Intermediate Similarity	NPC210192
0.8295	Intermediate Similarity	NPC3439
0.8295	Intermediate Similarity	NPC222004
0.8295	Intermediate Similarity	NPC218856
0.8295	Intermediate Similarity	NPC93962
0.8295	Intermediate Similarity	NPC285339
0.8295	Intermediate Similarity	NPC190629
0.8295	Intermediate Similarity	NPC202582
0.8295	Intermediate Similarity	NPC470258
0.8295	Intermediate Similarity	NPC469963
0.8295	Intermediate Similarity	NPC273295
0.8295	Intermediate Similarity	NPC469951
0.8295	Intermediate Similarity	NPC226788
0.8295	Intermediate Similarity	NPC210623
0.8293	Intermediate Similarity	NPC32152
0.8291	Intermediate Similarity	NPC241549
0.8291	Intermediate Similarity	NPC245115
0.8281	Intermediate Similarity	NPC216836
0.8281	Intermediate Similarity	NPC473134
0.8281	Intermediate Similarity	NPC210355
0.8281	Intermediate Similarity	NPC474119
0.8281	Intermediate Similarity	NPC469386
0.8279	Intermediate Similarity	NPC195466
0.8271	Intermediate Similarity	NPC302701

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 NPC212965 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	971
0.2-0.3	1835
0.3-0.4	2797
0.4-0.5	1567
0.5-0.6	1012
0.6-0.7	581
0.7-0.8	64
0.8-0.85	14
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9008	High Similarity	NPD4749	Approved
0.896	High Similarity	NPD6410	Clinical (unspecified phase)
0.873	High Similarity	NPD4625	Phase 3
0.8667	High Similarity	NPD1548	Phase 1
0.8492	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD1610	Phase 2
0.8359	Intermediate Similarity	NPD4908	Phase 1
0.8264	Intermediate Similarity	NPD6671	Approved
0.824	Intermediate Similarity	NPD422	Phase 1
0.8231	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD1613	Approved
0.808	Intermediate Similarity	NPD1778	Approved
0.8074	Intermediate Similarity	NPD6100	Approved
0.8074	Intermediate Similarity	NPD6099	Approved
0.8067	Intermediate Similarity	NPD4750	Phase 3
0.8051	Intermediate Similarity	NPD290	Approved
0.8015	Intermediate Similarity	NPD3027	Phase 3
0.7953	Intermediate Similarity	NPD1091	Approved
0.7939	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6696	Suspended
0.7863	Intermediate Similarity	NPD2861	Phase 2
0.7863	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD968	Approved
0.7778	Intermediate Similarity	NPD5124	Phase 1
0.7778	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD2684	Approved
0.7681	Intermediate Similarity	NPD1551	Phase 2
0.7627	Intermediate Similarity	NPD846	Approved
0.7627	Intermediate Similarity	NPD940	Approved
0.7597	Intermediate Similarity	NPD3496	Discontinued
0.7594	Intermediate Similarity	NPD3018	Phase 2
0.7589	Intermediate Similarity	NPD3892	Phase 2
0.7542	Intermediate Similarity	NPD1242	Phase 1
0.752	Intermediate Similarity	NPD1398	Phase 1
0.7518	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7447	Phase 1
0.75	Intermediate Similarity	NPD844	Approved
0.7482	Intermediate Similarity	NPD7033	Discontinued
0.7481	Intermediate Similarity	NPD2235	Phase 2
0.7481	Intermediate Similarity	NPD2231	Phase 2
0.748	Intermediate Similarity	NPD7340	Approved
0.7466	Intermediate Similarity	NPD1653	Approved
0.7445	Intermediate Similarity	NPD2238	Phase 2
0.744	Intermediate Similarity	NPD7843	Approved
0.7431	Intermediate Similarity	NPD7213	Phase 3
0.7431	Intermediate Similarity	NPD7212	Phase 2
0.7424	Intermediate Similarity	NPD2983	Phase 2
0.7424	Intermediate Similarity	NPD2982	Phase 2
0.7402	Intermediate Similarity	NPD7157	Approved
0.7394	Intermediate Similarity	NPD1652	Phase 2
0.7388	Intermediate Similarity	NPD6584	Phase 3
0.7385	Intermediate Similarity	NPD4626	Approved
0.7379	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8651	Approved
0.7368	Intermediate Similarity	NPD3225	Approved
0.736	Intermediate Similarity	NPD228	Approved
0.7348	Intermediate Similarity	NPD2981	Phase 2
0.7343	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1607	Approved
0.7324	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD4060	Phase 1
0.7313	Intermediate Similarity	NPD2797	Approved
0.7308	Intermediate Similarity	NPD5691	Approved
0.7305	Intermediate Similarity	NPD2796	Approved
0.7302	Intermediate Similarity	NPD821	Approved
0.7293	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD288	Approved
0.7259	Intermediate Similarity	NPD3690	Phase 2
0.7259	Intermediate Similarity	NPD3691	Phase 2
0.7254	Intermediate Similarity	NPD5762	Approved
0.7254	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD5763	Approved
0.7234	Intermediate Similarity	NPD1510	Phase 2
0.7222	Intermediate Similarity	NPD3750	Approved
0.7219	Intermediate Similarity	NPD2801	Approved
0.7219	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD1608	Approved
0.7218	Intermediate Similarity	NPD2230	Approved
0.7218	Intermediate Similarity	NPD2232	Approved
0.7218	Intermediate Similarity	NPD2233	Approved
0.7203	Intermediate Similarity	NPD1549	Phase 2
0.7194	Intermediate Similarity	NPD1240	Approved
0.7192	Intermediate Similarity	NPD1511	Approved
0.7192	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5585	Approved
0.7164	Intermediate Similarity	NPD6583	Phase 3
0.7164	Intermediate Similarity	NPD6582	Phase 2
0.7163	Intermediate Similarity	NPD2200	Suspended
0.7154	Intermediate Similarity	NPD9697	Approved
0.7153	Intermediate Similarity	NPD600	Approved
0.7153	Intermediate Similarity	NPD596	Approved
0.7153	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1934	Approved
0.7143	Intermediate Similarity	NPD5735	Approved
0.7143	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2557	Approved
0.7124	Intermediate Similarity	NPD3882	Suspended
0.7113	Intermediate Similarity	NPD4308	Phase 3
0.7103	Intermediate Similarity	NPD7466	Approved
0.7095	Intermediate Similarity	NPD1512	Approved
0.7092	Intermediate Similarity	NPD4097	Suspended
0.708	Intermediate Similarity	NPD1712	Approved
0.7071	Intermediate Similarity	NPD4140	Approved
0.7059	Intermediate Similarity	NPD5402	Approved
0.7055	Intermediate Similarity	NPD2677	Approved
0.705	Intermediate Similarity	NPD3268	Approved
0.705	Intermediate Similarity	NPD411	Approved
0.7047	Intermediate Similarity	NPD5403	Approved
0.7045	Intermediate Similarity	NPD3443	Approved
0.7045	Intermediate Similarity	NPD3444	Approved
0.7045	Intermediate Similarity	NPD1357	Approved
0.7045	Intermediate Similarity	NPD3445	Approved
0.7037	Intermediate Similarity	NPD5327	Phase 3
0.7027	Intermediate Similarity	NPD2533	Approved
0.7027	Intermediate Similarity	NPD2534	Approved
0.7027	Intermediate Similarity	NPD2532	Approved
0.702	Intermediate Similarity	NPD4675	Approved
0.702	Intermediate Similarity	NPD4380	Phase 2
0.702	Intermediate Similarity	NPD4678	Approved
0.7015	Intermediate Similarity	NPD1611	Approved
0.7014	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD3540	Phase 1
0.7014	Intermediate Similarity	NPD6004	Phase 3
0.7014	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6002	Phase 3
0.7014	Intermediate Similarity	NPD6005	Phase 3
0.7009	Intermediate Similarity	NPD9365	Approved
0.7007	Intermediate Similarity	NPD558	Phase 2
0.7	Intermediate Similarity	NPD709	Approved
0.7	Intermediate Similarity	NPD840	Approved
0.7	Intermediate Similarity	NPD839	Approved
0.6993	Remote Similarity	NPD7819	Suspended
0.6992	Remote Similarity	NPD17	Approved
0.6992	Remote Similarity	NPD6516	Phase 2
0.6992	Remote Similarity	NPD5846	Approved
0.6986	Remote Similarity	NPD4628	Phase 3
0.6977	Remote Similarity	NPD5283	Phase 1
0.6975	Remote Similarity	NPD2934	Approved
0.6975	Remote Similarity	NPD2933	Approved
0.6972	Remote Similarity	NPD6653	Approved
0.6972	Remote Similarity	NPD6353	Approved
0.6972	Remote Similarity	NPD3052	Approved
0.6972	Remote Similarity	NPD3054	Approved
0.697	Remote Similarity	NPD1182	Approved
0.6968	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2424	Discontinued
0.6963	Remote Similarity	NPD9717	Approved
0.696	Remote Similarity	NPD3134	Approved
0.6959	Remote Similarity	NPD6799	Approved
0.6957	Remote Similarity	NPD2237	Approved
0.695	Remote Similarity	NPD1558	Phase 1
0.6948	Remote Similarity	NPD3817	Phase 2
0.6948	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3539	Phase 1
0.6943	Remote Similarity	NPD6959	Discontinued
0.6934	Remote Similarity	NPD1203	Approved
0.6929	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1048	Approved
0.6929	Remote Similarity	NPD1296	Phase 2
0.6923	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4536	Approved
0.6923	Remote Similarity	NPD4538	Approved
0.6918	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6166	Phase 2
0.6918	Remote Similarity	NPD6674	Discontinued
0.6917	Remote Similarity	NPD3049	Approved
0.6917	Remote Similarity	NPD2859	Approved
0.6917	Remote Similarity	NPD2860	Approved
0.6913	Remote Similarity	NPD5401	Approved
0.6912	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4359	Approved
0.6912	Remote Similarity	NPD3685	Discontinued
0.6911	Remote Similarity	NPD291	Approved
0.6908	Remote Similarity	NPD6599	Discontinued
0.6903	Remote Similarity	NPD7768	Phase 2
0.6903	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7635	Approved
0.6899	Remote Similarity	NPD5535	Approved
0.6894	Remote Similarity	NPD5844	Phase 1
0.6894	Remote Similarity	NPD7054	Approved
0.6892	Remote Similarity	NPD6667	Approved
0.6892	Remote Similarity	NPD6815	Approved
0.6892	Remote Similarity	NPD6666	Approved
0.6889	Remote Similarity	NPD3705	Approved
0.6885	Remote Similarity	NPD3020	Approved
0.6884	Remote Similarity	NPD4624	Approved
0.6879	Remote Similarity	NPD6746	Phase 2
0.6875	Remote Similarity	NPD2155	Approved
0.6875	Remote Similarity	NPD3748	Approved
0.6875	Remote Similarity	NPD2156	Approved
0.6875	Remote Similarity	NPD2154	Approved
0.6871	Remote Similarity	NPD6559	Discontinued
0.6866	Remote Similarity	NPD2667	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