NPASS Compound

Structure

CID120638 OpenBabel06191715472D 25 26 0 0 1 0 0 0 0 0999 V2000 -5.6263 1.8108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8510 0.5860 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 -2.5391 -0.0517 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 -4.7297 -1.5353 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 -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 -5.8851 0.8449 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 -5.1780 0.1378 0.0000 C 0 0 3 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 -4.2121 0.3966 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 15 2 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 16 2 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 22 1 0 0 0 0 12 22 1 0 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 21 2 0 0 0 0 15 19 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 22 5 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:	4.849
LogD:	4.296
LogS:	-4.652
# 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:	3.999
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:	-4.756
MDCK Permeability:	2.935743577836547e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.083
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.556
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	98.34577178955078%
Volume Distribution (VD):	0.483
Pgp-substrate:	1.197850227355957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.667
CYP1A2-substrate:	0.709
CYP2C19-inhibitor:	0.259
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.24
CYP2C9-substrate:	0.881
CYP2D6-inhibitor:	0.932
CYP2D6-substrate:	0.733
CYP3A4-inhibitor:	0.889
CYP3A4-substrate:	0.356

ADMET: Excretion

Clearance (CL):	7.664
Half-life (T1/2):	0.355

ADMET: Toxicity

hERG Blockers:	0.149
Human Hepatotoxicity (H-HT):	0.855
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.894
Carcinogencity:	0.099
Eye Corrosion:	0.004
Eye Irritation:	0.216
Respiratory Toxicity:	0.762

Download Data

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

Natural Product: NPC120638

Natural Product ID:	NPC120638
*Common Name:**	Daurichromene A
IUPAC Name:	(2R)-2-[(3E)-7-hydroxy-4,8-dimethylnona-3,8-dienyl]-2,7-dimethylchromen-5-ol
Synonyms:
Standard InCHIKey:	WZLRGCNVNAHRNP-HKXAYFEUSA-N
Standard InCHI:	InChI=1S/C22H30O3/c1-15(2)19(23)9-8-16(3)7-6-11-22(5)12-10-18-20(24)13-17(4)14-21(18)25-22/h7,10,12-14,19,23-24H,1,6,8-9,11H2,2-5H3/b16-7+/t19?,22-/m1/s1
SMILES:	C/C(=CCC[C@]1(C)C=Cc2c(O1)cc(cc2O)C)/CCC(C(=C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487206
PubChem CID:	10043035
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans

*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	=	1.6	uL	PMID[564925]

☑ 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 NPC120638 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	344
0.1-0.2	1515
0.2-0.3	4860
0.3-0.4	13154
0.4-0.5	5052
0.5-0.6	5123
0.6-0.7	8937
0.7-0.8	3175
0.8-0.85	469
0.85-0.9	51
0.9-0.95	10
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9913	High Similarity	NPC212965
0.9746	High Similarity	NPC476254
0.9746	High Similarity	NPC131397
0.9652	High Similarity	NPC85895
0.9652	High Similarity	NPC137294
0.9487	High Similarity	NPC218753
0.9333	High Similarity	NPC270030
0.9187	High Similarity	NPC211179
0.9187	High Similarity	NPC38604
0.9113	High Similarity	NPC472795
0.9113	High Similarity	NPC472796
0.9113	High Similarity	NPC472797
0.9008	High Similarity	NPC74137
0.9008	High Similarity	NPC77789
0.9008	High Similarity	NPC18128
0.8992	High Similarity	NPC184302
0.8952	High Similarity	NPC46978
0.8934	High Similarity	NPC96940
0.8908	High Similarity	NPC190514
0.8824	High Similarity	NPC33270
0.8824	High Similarity	NPC69261
0.8819	High Similarity	NPC472590
0.8819	High Similarity	NPC82503
0.875	High Similarity	NPC472798
0.874	High Similarity	NPC474481
0.8739	High Similarity	NPC150624
0.872	High Similarity	NPC476006
0.8699	High Similarity	NPC36016
0.8699	High Similarity	NPC100099
0.8682	High Similarity	NPC36661
0.8678	High Similarity	NPC295259
0.8661	High Similarity	NPC222108
0.8661	High Similarity	NPC96719
0.8661	High Similarity	NPC16577
0.8655	High Similarity	NPC53906
0.8655	High Similarity	NPC808
0.8651	High Similarity	NPC149796
0.864	High Similarity	NPC293801
0.8632	High Similarity	NPC255068
0.8629	High Similarity	NPC38761
0.8629	High Similarity	NPC261992
0.8629	High Similarity	NPC76465
0.8626	High Similarity	NPC472800
0.8626	High Similarity	NPC476698
0.8626	High Similarity	NPC327735
0.8626	High Similarity	NPC126101
0.8595	High Similarity	NPC74821
0.8595	High Similarity	NPC283616
0.8583	High Similarity	NPC274717
0.8583	High Similarity	NPC203113
0.8571	High Similarity	NPC228287
0.8571	High Similarity	NPC276212
0.8571	High Similarity	NPC276737
0.8571	High Similarity	NPC22610
0.8571	High Similarity	NPC180508
0.8561	High Similarity	NPC134260
0.856	High Similarity	NPC197351
0.856	High Similarity	NPC86502
0.856	High Similarity	NPC106914
0.856	High Similarity	NPC246648
0.856	High Similarity	NPC134195
0.8559	High Similarity	NPC474920
0.8548	High Similarity	NPC188997
0.8547	High Similarity	NPC106141
0.8547	High Similarity	NPC94045
0.8547	High Similarity	NPC168657
0.8538	High Similarity	NPC475840
0.8538	High Similarity	NPC469610
0.8537	High Similarity	NPC102639
0.8522	High Similarity	NPC164576
0.8516	High Similarity	NPC134360
0.8512	High Similarity	NPC244816
0.8512	High Similarity	NPC50521
0.8512	High Similarity	NPC221549
0.8512	High Similarity	NPC15860
0.8512	High Similarity	NPC219070
0.8512	High Similarity	NPC127894
0.8512	High Similarity	NPC470759
0.8512	High Similarity	NPC474933
0.8504	High Similarity	NPC121740
0.8504	High Similarity	NPC224774
0.8504	High Similarity	NPC258567
0.85	High Similarity	NPC185541
0.85	High Similarity	NPC464
0.8492	Intermediate Similarity	NPC285040
0.8492	Intermediate Similarity	NPC188022
0.8492	Intermediate Similarity	NPC17809
0.8492	Intermediate Similarity	NPC102540
0.8492	Intermediate Similarity	NPC103420
0.8492	Intermediate Similarity	NPC105031
0.848	Intermediate Similarity	NPC474160
0.8468	Intermediate Similarity	NPC75713
0.8468	Intermediate Similarity	NPC54972
0.8468	Intermediate Similarity	NPC476633
0.8462	Intermediate Similarity	NPC469611
0.8455	Intermediate Similarity	NPC258979
0.8455	Intermediate Similarity	NPC8283
0.8455	Intermediate Similarity	NPC93398
0.845	Intermediate Similarity	NPC229231
0.845	Intermediate Similarity	NPC472338
0.8438	Intermediate Similarity	NPC469453
0.8438	Intermediate Similarity	NPC222572
0.8438	Intermediate Similarity	NPC87224
0.843	Intermediate Similarity	NPC229147
0.843	Intermediate Similarity	NPC141090
0.843	Intermediate Similarity	NPC290470
0.843	Intermediate Similarity	NPC114064
0.843	Intermediate Similarity	NPC85292
0.843	Intermediate Similarity	NPC54507
0.843	Intermediate Similarity	NPC154256
0.8425	Intermediate Similarity	NPC283049
0.8425	Intermediate Similarity	NPC26879
0.8425	Intermediate Similarity	NPC244364
0.8425	Intermediate Similarity	NPC50315
0.8425	Intermediate Similarity	NPC230479
0.8417	Intermediate Similarity	NPC161696
0.8413	Intermediate Similarity	NPC159132
0.8409	Intermediate Similarity	NPC61946
0.8409	Intermediate Similarity	NPC151224
0.8409	Intermediate Similarity	NPC164787
0.8409	Intermediate Similarity	NPC472337
0.8403	Intermediate Similarity	NPC280606
0.84	Intermediate Similarity	NPC57199
0.8397	Intermediate Similarity	NPC37196
0.8397	Intermediate Similarity	NPC269528
0.8397	Intermediate Similarity	NPC168059
0.8397	Intermediate Similarity	NPC11060
0.8397	Intermediate Similarity	NPC94236
0.8397	Intermediate Similarity	NPC229442
0.8387	Intermediate Similarity	NPC473875
0.8387	Intermediate Similarity	NPC199023
0.8387	Intermediate Similarity	NPC96423
0.8385	Intermediate Similarity	NPC244888
0.8385	Intermediate Similarity	NPC211413
0.8385	Intermediate Similarity	NPC472597
0.8385	Intermediate Similarity	NPC103799
0.8385	Intermediate Similarity	NPC68205
0.8385	Intermediate Similarity	NPC160623
0.8385	Intermediate Similarity	NPC164804
0.8385	Intermediate Similarity	NPC8899
0.8385	Intermediate Similarity	NPC162801
0.8385	Intermediate Similarity	NPC118683
0.8385	Intermediate Similarity	NPC293203
0.8374	Intermediate Similarity	NPC471449
0.8372	Intermediate Similarity	NPC218856
0.8372	Intermediate Similarity	NPC285339
0.8372	Intermediate Similarity	NPC273295
0.8372	Intermediate Similarity	NPC226788
0.8372	Intermediate Similarity	NPC190629
0.8372	Intermediate Similarity	NPC470258
0.8372	Intermediate Similarity	NPC210623
0.8372	Intermediate Similarity	NPC469951
0.8372	Intermediate Similarity	NPC222004
0.8372	Intermediate Similarity	NPC469963
0.8372	Intermediate Similarity	NPC202582
0.8372	Intermediate Similarity	NPC3439
0.837	Intermediate Similarity	NPC210192
0.8362	Intermediate Similarity	NPC473653
0.8359	Intermediate Similarity	NPC236760
0.8359	Intermediate Similarity	NPC469386
0.8359	Intermediate Similarity	NPC473221
0.8359	Intermediate Similarity	NPC474119
0.8347	Intermediate Similarity	NPC167934
0.8347	Intermediate Similarity	NPC473718
0.8347	Intermediate Similarity	NPC301321
0.8346	Intermediate Similarity	NPC16435
0.8346	Intermediate Similarity	NPC227503
0.8346	Intermediate Similarity	NPC472336
0.8346	Intermediate Similarity	NPC472334
0.8346	Intermediate Similarity	NPC230734
0.8346	Intermediate Similarity	NPC12308
0.8346	Intermediate Similarity	NPC302701
0.8346	Intermediate Similarity	NPC306441
0.8346	Intermediate Similarity	NPC141717
0.8346	Intermediate Similarity	NPC269091
0.8346	Intermediate Similarity	NPC474639
0.8333	Intermediate Similarity	NPC473107
0.8333	Intermediate Similarity	NPC296915
0.8333	Intermediate Similarity	NPC95168
0.8333	Intermediate Similarity	NPC97834
0.8333	Intermediate Similarity	NPC198154
0.8333	Intermediate Similarity	NPC225696
0.8333	Intermediate Similarity	NPC223008
0.8333	Intermediate Similarity	NPC319803
0.8333	Intermediate Similarity	NPC115335
0.8321	Intermediate Similarity	NPC161203
0.8321	Intermediate Similarity	NPC184447
0.8321	Intermediate Similarity	NPC35932
0.8321	Intermediate Similarity	NPC16208
0.8321	Intermediate Similarity	NPC13005
0.8321	Intermediate Similarity	NPC160991
0.8321	Intermediate Similarity	NPC7903
0.832	Intermediate Similarity	NPC193364
0.8319	Intermediate Similarity	NPC296920
0.8319	Intermediate Similarity	NPC90520
0.8308	Intermediate Similarity	NPC91291
0.8308	Intermediate Similarity	NPC113098
0.8308	Intermediate Similarity	NPC474491
0.8308	Intermediate Similarity	NPC262606
0.8308	Intermediate Similarity	NPC220935

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 NPC120638 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	923
0.2-0.3	1897
0.3-0.4	2787
0.4-0.5	1545
0.5-0.6	1019
0.6-0.7	583
0.7-0.8	67
0.8-0.85	12
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8934	High Similarity	NPD4749	Approved
0.8889	High Similarity	NPD6410	Clinical (unspecified phase)
0.8661	High Similarity	NPD4625	Phase 3
0.8595	High Similarity	NPD1548	Phase 1
0.8425	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.832	Intermediate Similarity	NPD1610	Phase 2
0.8295	Intermediate Similarity	NPD4908	Phase 1
0.8197	Intermediate Similarity	NPD6671	Approved
0.8182	Intermediate Similarity	NPD1613	Approved
0.8182	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD422	Phase 1
0.8168	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD290	Approved
0.8092	Intermediate Similarity	NPD3027	Phase 3
0.8031	Intermediate Similarity	NPD1091	Approved
0.8016	Intermediate Similarity	NPD1778	Approved
0.8015	Intermediate Similarity	NPD6100	Approved
0.8015	Intermediate Similarity	NPD6099	Approved
0.8	Intermediate Similarity	NPD4750	Phase 3
0.7939	Intermediate Similarity	NPD2861	Phase 2
0.7879	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD5124	Phase 1
0.7846	Intermediate Similarity	NPD6696	Suspended
0.7803	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD968	Approved
0.7626	Intermediate Similarity	NPD1551	Phase 2
0.7623	Intermediate Similarity	NPD2684	Approved
0.7589	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD846	Approved
0.7563	Intermediate Similarity	NPD940	Approved
0.7557	Intermediate Similarity	NPD2231	Phase 2
0.7557	Intermediate Similarity	NPD2235	Phase 2
0.7554	Intermediate Similarity	NPD7033	Discontinued
0.7538	Intermediate Similarity	NPD3496	Discontinued
0.7537	Intermediate Similarity	NPD3018	Phase 2
0.7535	Intermediate Similarity	NPD3892	Phase 2
0.7534	Intermediate Similarity	NPD1653	Approved
0.7518	Intermediate Similarity	NPD2238	Phase 2
0.75	Intermediate Similarity	NPD7212	Phase 2
0.75	Intermediate Similarity	NPD7213	Phase 3
0.7479	Intermediate Similarity	NPD1242	Phase 1
0.7465	Intermediate Similarity	NPD1652	Phase 2
0.746	Intermediate Similarity	NPD1398	Phase 1
0.7448	Intermediate Similarity	NPD7447	Phase 1
0.7448	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD844	Approved
0.7422	Intermediate Similarity	NPD7340	Approved
0.7381	Intermediate Similarity	NPD7843	Approved
0.7376	Intermediate Similarity	NPD2796	Approved
0.7368	Intermediate Similarity	NPD2982	Phase 2
0.7368	Intermediate Similarity	NPD2983	Phase 2
0.7344	Intermediate Similarity	NPD7157	Approved
0.7333	Intermediate Similarity	NPD6584	Phase 3
0.7329	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD4626	Approved
0.7324	Intermediate Similarity	NPD5763	Approved
0.7324	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD5762	Approved
0.7313	Intermediate Similarity	NPD8651	Approved
0.7313	Intermediate Similarity	NPD3225	Approved
0.7302	Intermediate Similarity	NPD228	Approved
0.7293	Intermediate Similarity	NPD2981	Phase 2
0.7292	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1607	Approved
0.7285	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1549	Phase 2
0.7266	Intermediate Similarity	NPD4060	Phase 1
0.7259	Intermediate Similarity	NPD2797	Approved
0.7252	Intermediate Similarity	NPD5691	Approved
0.7244	Intermediate Similarity	NPD821	Approved
0.7239	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD288	Approved
0.7226	Intermediate Similarity	NPD600	Approved
0.7226	Intermediate Similarity	NPD596	Approved
0.7219	Intermediate Similarity	NPD1934	Approved
0.7214	Intermediate Similarity	NPD5735	Approved
0.7206	Intermediate Similarity	NPD3690	Phase 2
0.7206	Intermediate Similarity	NPD3691	Phase 2
0.7183	Intermediate Similarity	NPD1510	Phase 2
0.7172	Intermediate Similarity	NPD3750	Approved
0.7171	Intermediate Similarity	NPD2801	Approved
0.7164	Intermediate Similarity	NPD2233	Approved
0.7164	Intermediate Similarity	NPD1608	Approved
0.7164	Intermediate Similarity	NPD2232	Approved
0.7164	Intermediate Similarity	NPD2230	Approved
0.7143	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4140	Approved
0.7143	Intermediate Similarity	NPD1240	Approved
0.7143	Intermediate Similarity	NPD1511	Approved
0.7124	Intermediate Similarity	NPD5402	Approved
0.7123	Intermediate Similarity	NPD2677	Approved
0.7121	Intermediate Similarity	NPD1357	Approved
0.7121	Intermediate Similarity	NPD5585	Approved
0.7114	Intermediate Similarity	NPD5403	Approved
0.7113	Intermediate Similarity	NPD2200	Suspended
0.7111	Intermediate Similarity	NPD6582	Phase 2
0.7111	Intermediate Similarity	NPD5327	Phase 3
0.7111	Intermediate Similarity	NPD6583	Phase 3
0.7101	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD9697	Approved
0.7095	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4380	Phase 2
0.7083	Intermediate Similarity	NPD6002	Phase 3
0.7083	Intermediate Similarity	NPD6005	Phase 3
0.7083	Intermediate Similarity	NPD6004	Phase 3
0.7083	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD558	Phase 2
0.7078	Intermediate Similarity	NPD3882	Suspended
0.7077	Intermediate Similarity	NPD2557	Approved
0.7071	Intermediate Similarity	NPD840	Approved
0.7071	Intermediate Similarity	NPD839	Approved
0.7063	Intermediate Similarity	NPD4308	Phase 3
0.7055	Intermediate Similarity	NPD7466	Approved
0.7055	Intermediate Similarity	NPD4628	Phase 3
0.7047	Intermediate Similarity	NPD1512	Approved
0.7042	Intermediate Similarity	NPD6353	Approved
0.7042	Intermediate Similarity	NPD4097	Suspended
0.7042	Intermediate Similarity	NPD3052	Approved
0.7042	Intermediate Similarity	NPD6653	Approved
0.7042	Intermediate Similarity	NPD3054	Approved
0.7034	Intermediate Similarity	NPD2424	Discontinued
0.7032	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1712	Approved
0.7013	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6959	Discontinued
0.7	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3268	Approved
0.7	Intermediate Similarity	NPD411	Approved
0.7	Intermediate Similarity	NPD1048	Approved
0.6993	Remote Similarity	NPD4536	Approved
0.6993	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4538	Approved
0.6992	Remote Similarity	NPD3445	Approved
0.6992	Remote Similarity	NPD291	Approved
0.6992	Remote Similarity	NPD3444	Approved
0.6992	Remote Similarity	NPD3443	Approved
0.6986	Remote Similarity	NPD6674	Discontinued
0.6985	Remote Similarity	NPD3685	Discontinued
0.6981	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6166	Phase 2
0.6981	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5401	Approved
0.698	Remote Similarity	NPD2533	Approved
0.698	Remote Similarity	NPD2532	Approved
0.698	Remote Similarity	NPD2534	Approved
0.6974	Remote Similarity	NPD4675	Approved
0.6974	Remote Similarity	NPD4678	Approved
0.6968	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3540	Phase 1
0.6963	Remote Similarity	NPD1611	Approved
0.6957	Remote Similarity	NPD5844	Phase 1
0.6957	Remote Similarity	NPD7054	Approved
0.6949	Remote Similarity	NPD9365	Approved
0.6948	Remote Similarity	NPD7819	Suspended
0.6947	Remote Similarity	NPD709	Approved
0.6944	Remote Similarity	NPD2155	Approved
0.6944	Remote Similarity	NPD2156	Approved
0.6944	Remote Similarity	NPD2154	Approved
0.694	Remote Similarity	NPD6516	Phase 2
0.694	Remote Similarity	NPD2554	Approved
0.694	Remote Similarity	NPD17	Approved
0.694	Remote Similarity	NPD2556	Approved
0.694	Remote Similarity	NPD5846	Approved
0.6933	Remote Similarity	NPD6559	Discontinued
0.6929	Remote Similarity	NPD3179	Approved
0.6929	Remote Similarity	NPD3180	Approved
0.6928	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7075	Discontinued
0.6923	Remote Similarity	NPD5283	Phase 1
0.6917	Remote Similarity	NPD1182	Approved
0.6917	Remote Similarity	NPD2934	Approved
0.6917	Remote Similarity	NPD2933	Approved
0.6914	Remote Similarity	NPD7472	Approved
0.6913	Remote Similarity	NPD6799	Approved
0.6912	Remote Similarity	NPD9717	Approved
0.6911	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2237	Approved
0.6905	Remote Similarity	NPD3134	Approved
0.6903	Remote Similarity	NPD3817	Phase 2
0.6901	Remote Similarity	NPD3620	Phase 2
0.6901	Remote Similarity	NPD1558	Phase 1
0.6901	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3539	Phase 1
0.6897	Remote Similarity	NPD6032	Approved
0.6894	Remote Similarity	NPD3818	Discontinued
0.6884	Remote Similarity	NPD1794	Approved
0.6884	Remote Similarity	NPD1203	Approved
0.6883	Remote Similarity	NPD6801	Discontinued
0.6883	Remote Similarity	NPD37	Approved
0.6879	Remote Similarity	NPD1296	Phase 2
0.6879	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6798	Discontinued
0.6871	Remote Similarity	NPD5177	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data