NPASS Compound

Structure

CID37139 OpenBabel06191715362D 27 28 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 -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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 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 -3.4641 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 2 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 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 1 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 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 15 2 0 0 0 0 9 16 1 0 0 0 0 10 16 2 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 23 1 0 0 0 0 13 23 1 0 0 0 0 14 17 2 0 0 0 0 14 19 1 0 0 0 0 17 20 1 0 0 0 0 18 19 2 0 0 0 0 18 21 1 0 0 0 0 19 27 1 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 21 24 1 0 0 0 0 22 25 2 0 0 0 0 22 26 1 0 0 0 0 23 5 1 1 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.21
Volume:	405.957
LogP:	6.753
LogD:	4.808
LogS:	-3.322
# Rotatable Bonds:	7
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.575
Synthetic Accessibility Score:	3.607
Fsp3:	0.435
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.825
MDCK Permeability:	2.5826639102888294e-05
Pgp-inhibitor:	0.043
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	99.40192413330078%
Volume Distribution (VD):	0.513
Pgp-substrate:	2.052663803100586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.166
CYP1A2-substrate:	0.262
CYP2C19-inhibitor:	0.075
CYP2C19-substrate:	0.138
CYP2C9-inhibitor:	0.604
CYP2C9-substrate:	0.397
CYP2D6-inhibitor:	0.887
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.389
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	2.491
Half-life (T1/2):	0.363

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.949
Drug-inuced Liver Injury (DILI):	0.789
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.534
Maximum Recommended Daily Dose:	0.133
Skin Sensitization:	0.88
Carcinogencity:	0.233
Eye Corrosion:	0.003
Eye Irritation:	0.049
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC37139

Natural Product ID:	NPC37139
*Common Name:**	Daurichromenic Acid
IUPAC Name:	(2S)-2-[(3E)-4,8-dimethylnona-3,7-dienyl]-5-hydroxy-2,7-dimethylchromene-6-carboxylic acid
Synonyms:	Daurichromenic Acid
Standard InCHIKey:	UYLFTJMQPWWDCW-MVLVPLOLSA-N
Standard InCHI:	InChI=1S/C23H30O4/c1-15(2)8-6-9-16(3)10-7-12-23(5)13-11-18-19(27-23)14-17(4)20(21(18)24)22(25)26/h8,10-11,13-14,24H,6-7,9,12H2,1-5H3,(H,25,26)/b16-10+/t23-/m0/s1
SMILES:	C/C(=CCC[C@@]1(C)C=Cc2c(O1)cc(c(c2O)C(=O)O)C)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1171643
PubChem CID:	6475854
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
EC50	1
IC50	1
Others	1

Activity Type	# Activity
Individual Protein	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	15.0	nM	PMID[497544]
NPT27	Others	Unspecified		TI	=	3710.0	n.a.	PMID[497544]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	IC50	=	24700.0	nM	PMID[497545]

☑ 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 NPC37139 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	376
0.1-0.2	1609
0.2-0.3	3849
0.3-0.4	9007
0.4-0.5	9372
0.5-0.6	3489
0.6-0.7	5944
0.7-0.8	6276
0.8-0.85	2093
0.85-0.9	612
0.9-0.95	62
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.986	High Similarity	NPC158866
0.9586	High Similarity	NPC150928
0.9583	High Similarity	NPC105415
0.9517	High Similarity	NPC233267
0.9517	High Similarity	NPC291049
0.9456	High Similarity	NPC217447
0.9456	High Similarity	NPC271681
0.9444	High Similarity	NPC225173
0.9444	High Similarity	NPC163846
0.9392	High Similarity	NPC472799
0.9388	High Similarity	NPC133856
0.9379	High Similarity	NPC125801
0.9324	High Similarity	NPC273483
0.9296	High Similarity	NPC165172
0.9272	High Similarity	NPC474373
0.9267	High Similarity	NPC4547
0.9262	High Similarity	NPC210942
0.9262	High Similarity	NPC169990
0.9262	High Similarity	NPC329844
0.9252	High Similarity	NPC10027
0.9252	High Similarity	NPC97029
0.9252	High Similarity	NPC97028
0.9252	High Similarity	NPC288036
0.9252	High Similarity	NPC65775
0.9252	High Similarity	NPC65589
0.9252	High Similarity	NPC158338
0.9252	High Similarity	NPC100985
0.9241	High Similarity	NPC29577
0.9241	High Similarity	NPC312789
0.9241	High Similarity	NPC134621
0.92	High Similarity	NPC149618
0.92	High Similarity	NPC89625
0.9184	High Similarity	NPC256672
0.9184	High Similarity	NPC27221
0.9184	High Similarity	NPC7025
0.9178	High Similarity	NPC237208
0.9172	High Similarity	NPC66404
0.9172	High Similarity	NPC42540
0.9172	High Similarity	NPC95123
0.9172	High Similarity	NPC151607
0.9167	High Similarity	NPC105648
0.9167	High Similarity	NPC250755
0.9149	High Similarity	NPC50455
0.9139	High Similarity	NPC146211
0.9128	High Similarity	NPC478148
0.9128	High Similarity	NPC474417
0.9128	High Similarity	NPC258249
0.9128	High Similarity	NPC149526
0.9116	High Similarity	NPC7943
0.9116	High Similarity	NPC123202
0.9116	High Similarity	NPC22005
0.9103	High Similarity	NPC159721
0.9097	High Similarity	NPC1704
0.9097	High Similarity	NPC220106
0.9097	High Similarity	NPC67650
0.9091	High Similarity	NPC470668
0.9091	High Similarity	NPC470669
0.9091	High Similarity	NPC131130
0.9067	High Similarity	NPC175978
0.9054	High Similarity	NPC240253
0.9054	High Similarity	NPC471641
0.9054	High Similarity	NPC471642
0.9054	High Similarity	NPC240622
0.9048	High Similarity	NPC473927
0.9048	High Similarity	NPC154217
0.9034	High Similarity	NPC474385
0.9028	High Similarity	NPC23257
0.9014	High Similarity	NPC242712
0.9014	High Similarity	NPC158481
0.9007	High Similarity	NPC95842
0.9007	High Similarity	NPC477691
0.9007	High Similarity	NPC175943
0.9007	High Similarity	NPC280530
0.9007	High Similarity	NPC178964
0.9	High Similarity	NPC232645
0.9	High Similarity	NPC72958
0.8993	High Similarity	NPC269420
0.8993	High Similarity	NPC6923
0.8993	High Similarity	NPC329933
0.8986	High Similarity	NPC34802
0.8986	High Similarity	NPC137296
0.8986	High Similarity	NPC12305
0.8986	High Similarity	NPC140120
0.898	High Similarity	NPC196137
0.898	High Similarity	NPC469953
0.898	High Similarity	NPC32470
0.898	High Similarity	NPC75694
0.898	High Similarity	NPC1886
0.8973	High Similarity	NPC471731
0.8973	High Similarity	NPC472006
0.8973	High Similarity	NPC469542
0.8973	High Similarity	NPC84266
0.8973	High Similarity	NPC51106
0.8973	High Similarity	NPC36181
0.8966	High Similarity	NPC158634
0.8966	High Similarity	NPC475730
0.8966	High Similarity	NPC471587
0.8966	High Similarity	NPC221173
0.8966	High Similarity	NPC477272
0.8961	High Similarity	NPC143050
0.8958	High Similarity	NPC199458
0.8958	High Similarity	NPC57380
0.8958	High Similarity	NPC474487
0.8958	High Similarity	NPC470671
0.8958	High Similarity	NPC470672
0.8958	High Similarity	NPC183639
0.8958	High Similarity	NPC474504
0.8954	High Similarity	NPC263483
0.8951	High Similarity	NPC194579
0.8951	High Similarity	NPC174999
0.8951	High Similarity	NPC135837
0.8944	High Similarity	NPC182496
0.8944	High Similarity	NPC180905
0.894	High Similarity	NPC40356
0.894	High Similarity	NPC477690
0.894	High Similarity	NPC45934
0.894	High Similarity	NPC154683
0.894	High Similarity	NPC142527
0.894	High Similarity	NPC87708
0.8933	High Similarity	NPC309979
0.8933	High Similarity	NPC295036
0.8933	High Similarity	NPC227122
0.8933	High Similarity	NPC60413
0.8933	High Similarity	NPC307780
0.8933	High Similarity	NPC119929
0.8933	High Similarity	NPC325983
0.8926	High Similarity	NPC172329
0.8926	High Similarity	NPC208303
0.8926	High Similarity	NPC2569
0.8926	High Similarity	NPC161864
0.8919	High Similarity	NPC181388
0.8919	High Similarity	NPC267509
0.8919	High Similarity	NPC470322
0.8919	High Similarity	NPC260946
0.8919	High Similarity	NPC196114
0.8919	High Similarity	NPC470676
0.8919	High Similarity	NPC473135
0.8919	High Similarity	NPC57470
0.8919	High Similarity	NPC473132
0.8912	High Similarity	NPC219915
0.8912	High Similarity	NPC210425
0.8912	High Similarity	NPC189650
0.8912	High Similarity	NPC112791
0.8912	High Similarity	NPC277426
0.8912	High Similarity	NPC94794
0.8912	High Similarity	NPC196459
0.8912	High Similarity	NPC86373
0.8912	High Similarity	NPC11700
0.8912	High Similarity	NPC470296
0.8912	High Similarity	NPC280404
0.8912	High Similarity	NPC188632
0.8912	High Similarity	NPC87609
0.8904	High Similarity	NPC147688
0.8904	High Similarity	NPC205006
0.8904	High Similarity	NPC470555
0.8904	High Similarity	NPC94076
0.8904	High Similarity	NPC471733
0.8904	High Similarity	NPC469579
0.8904	High Similarity	NPC64908
0.8904	High Similarity	NPC96692
0.8904	High Similarity	NPC156590
0.8904	High Similarity	NPC182255
0.8904	High Similarity	NPC118840
0.8897	High Similarity	NPC96565
0.8897	High Similarity	NPC303633
0.8897	High Similarity	NPC216978
0.8897	High Similarity	NPC220062
0.8897	High Similarity	NPC301217
0.8897	High Similarity	NPC472601
0.8897	High Similarity	NPC55018
0.8897	High Similarity	NPC19476
0.8897	High Similarity	NPC241975
0.8897	High Similarity	NPC472600
0.8897	High Similarity	NPC472343
0.8889	High Similarity	NPC138047
0.8889	High Similarity	NPC131782
0.8889	High Similarity	NPC332594
0.8889	High Similarity	NPC474624
0.8882	High Similarity	NPC214632
0.8881	High Similarity	NPC151113
0.8881	High Similarity	NPC118919
0.8881	High Similarity	NPC101752
0.8873	High Similarity	NPC108113
0.8873	High Similarity	NPC93756
0.8867	High Similarity	NPC469932
0.8867	High Similarity	NPC473978
0.8867	High Similarity	NPC70764
0.8867	High Similarity	NPC474052
0.8861	High Similarity	NPC76647
0.8859	High Similarity	NPC297886
0.8859	High Similarity	NPC180477
0.8859	High Similarity	NPC8817
0.8859	High Similarity	NPC142863
0.8859	High Similarity	NPC249942
0.8851	High Similarity	NPC472034
0.8851	High Similarity	NPC178627
0.8851	High Similarity	NPC470674
0.8851	High Similarity	NPC470673
0.8851	High Similarity	NPC469935
0.8851	High Similarity	NPC311741

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 NPC37139 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	1007
0.2-0.3	1631
0.3-0.4	2592
0.4-0.5	1859
0.5-0.6	1084
0.6-0.7	430
0.7-0.8	169
0.8-0.85	35
0.85-0.9	4
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD970	Clinical (unspecified phase)
0.898	High Similarity	NPD2534	Approved
0.898	High Similarity	NPD2532	Approved
0.898	High Similarity	NPD2533	Approved
0.8882	High Similarity	NPD7819	Suspended
0.8725	High Similarity	NPD4378	Clinical (unspecified phase)
0.8608	High Similarity	NPD6232	Discontinued
0.86	High Similarity	NPD7410	Clinical (unspecified phase)
0.8581	High Similarity	NPD3750	Approved
0.8456	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD7473	Discontinued
0.8428	Intermediate Similarity	NPD6959	Discontinued
0.8397	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD7411	Suspended
0.8377	Intermediate Similarity	NPD3226	Approved
0.8356	Intermediate Similarity	NPD1607	Approved
0.8354	Intermediate Similarity	NPD7075	Discontinued
0.8354	Intermediate Similarity	NPD3749	Approved
0.8323	Intermediate Similarity	NPD6599	Discontinued
0.8311	Intermediate Similarity	NPD2935	Discontinued
0.8311	Intermediate Similarity	NPD1551	Phase 2
0.8291	Intermediate Similarity	NPD7768	Phase 2
0.8289	Intermediate Similarity	NPD1511	Approved
0.828	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD2800	Approved
0.8267	Intermediate Similarity	NPD1243	Approved
0.8261	Intermediate Similarity	NPD5711	Approved
0.8261	Intermediate Similarity	NPD5710	Approved
0.8255	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD2346	Discontinued
0.8255	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD3748	Approved
0.8243	Intermediate Similarity	NPD1510	Phase 2
0.8232	Intermediate Similarity	NPD5844	Phase 1
0.8228	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD1240	Approved
0.8217	Intermediate Similarity	NPD6801	Discontinued
0.82	Intermediate Similarity	NPD1549	Phase 2
0.8188	Intermediate Similarity	NPD6099	Approved
0.8188	Intermediate Similarity	NPD2796	Approved
0.8188	Intermediate Similarity	NPD6100	Approved
0.8182	Intermediate Similarity	NPD1512	Approved
0.817	Intermediate Similarity	NPD6799	Approved
0.8165	Intermediate Similarity	NPD2801	Approved
0.816	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD2799	Discontinued
0.8113	Intermediate Similarity	NPD3817	Phase 2
0.8101	Intermediate Similarity	NPD1934	Approved
0.8089	Intermediate Similarity	NPD4380	Phase 2
0.8082	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD4625	Phase 3
0.8013	Intermediate Similarity	NPD920	Approved
0.7987	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD4628	Phase 3
0.7959	Intermediate Similarity	NPD411	Approved
0.7958	Intermediate Similarity	NPD422	Phase 1
0.795	Intermediate Similarity	NPD3882	Suspended
0.7947	Intermediate Similarity	NPD5405	Approved
0.7947	Intermediate Similarity	NPD5404	Approved
0.7947	Intermediate Similarity	NPD5406	Approved
0.7947	Intermediate Similarity	NPD5408	Approved
0.7935	Intermediate Similarity	NPD7390	Discontinued
0.7902	Intermediate Similarity	NPD9717	Approved
0.7901	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD4308	Phase 3
0.787	Intermediate Similarity	NPD6559	Discontinued
0.7867	Intermediate Similarity	NPD6651	Approved
0.7862	Intermediate Similarity	NPD1203	Approved
0.7853	Intermediate Similarity	NPD919	Approved
0.784	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD2313	Discontinued
0.7826	Intermediate Similarity	NPD1465	Phase 2
0.7817	Intermediate Similarity	NPD4626	Approved
0.7811	Intermediate Similarity	NPD5953	Discontinued
0.7799	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1608	Approved
0.774	Intermediate Similarity	NPD2797	Approved
0.7738	Intermediate Similarity	NPD3818	Discontinued
0.7725	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6166	Phase 2
0.7724	Intermediate Similarity	NPD4749	Approved
0.7718	Intermediate Similarity	NPD3268	Approved
0.7697	Intermediate Similarity	NPD5494	Approved
0.7692	Intermediate Similarity	NPD7286	Phase 2
0.7692	Intermediate Similarity	NPD7054	Approved
0.7682	Intermediate Similarity	NPD5124	Phase 1
0.7682	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD447	Suspended
0.7673	Intermediate Similarity	NPD5403	Approved
0.7671	Intermediate Similarity	NPD1283	Approved
0.767	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD5402	Approved
0.7669	Intermediate Similarity	NPD4288	Approved
0.7662	Intermediate Similarity	NPD2344	Approved
0.7658	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7472	Approved
0.7647	Intermediate Similarity	NPD7033	Discontinued
0.7647	Intermediate Similarity	NPD7074	Phase 3
0.7628	Intermediate Similarity	NPD7003	Approved
0.7622	Intermediate Similarity	NPD5691	Approved
0.7616	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4307	Phase 2
0.7605	Intermediate Similarity	NPD7229	Phase 3
0.7602	Intermediate Similarity	NPD6797	Phase 2
0.76	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3764	Approved
0.76	Intermediate Similarity	NPD1296	Phase 2
0.7584	Intermediate Similarity	NPD6832	Phase 2
0.7569	Intermediate Similarity	NPD17	Approved
0.7566	Intermediate Similarity	NPD230	Phase 1
0.7558	Intermediate Similarity	NPD7251	Discontinued
0.7547	Intermediate Similarity	NPD5401	Approved
0.7529	Intermediate Similarity	NPD7177	Discontinued
0.7514	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD943	Approved
0.7483	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD8312	Approved
0.7471	Intermediate Similarity	NPD8313	Approved
0.7468	Intermediate Similarity	NPD2309	Approved
0.7466	Intermediate Similarity	NPD1281	Approved
0.7466	Intermediate Similarity	NPD1201	Approved
0.7451	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2798	Approved
0.7448	Intermediate Similarity	NPD1778	Approved
0.744	Intermediate Similarity	NPD1247	Approved
0.744	Intermediate Similarity	NPD7199	Phase 2
0.7432	Intermediate Similarity	NPD3225	Approved
0.7431	Intermediate Similarity	NPD9545	Approved
0.7419	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD9493	Approved
0.7391	Intermediate Similarity	NPD6273	Approved
0.7386	Intermediate Similarity	NPD2979	Phase 3
0.7383	Intermediate Similarity	NPD1164	Approved
0.7383	Intermediate Similarity	NPD3267	Approved
0.7383	Intermediate Similarity	NPD3266	Approved
0.7383	Intermediate Similarity	NPD1470	Approved
0.7372	Intermediate Similarity	NPD4476	Approved
0.7372	Intermediate Similarity	NPD4477	Approved
0.7362	Intermediate Similarity	NPD7458	Discontinued
0.736	Intermediate Similarity	NPD4287	Approved
0.736	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3926	Phase 2
0.7351	Intermediate Similarity	NPD4908	Phase 1
0.7346	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD37	Approved
0.7325	Intermediate Similarity	NPD1471	Phase 3
0.7321	Intermediate Similarity	NPD6234	Discontinued
0.7315	Intermediate Similarity	NPD6696	Suspended
0.7305	Intermediate Similarity	NPD4967	Phase 2
0.7305	Intermediate Similarity	NPD4965	Approved
0.7305	Intermediate Similarity	NPD4966	Approved
0.7299	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7783	Phase 2
0.7261	Intermediate Similarity	NPD2438	Suspended
0.726	Intermediate Similarity	NPD1651	Approved
0.7258	Intermediate Similarity	NPD7435	Discontinued
0.7247	Intermediate Similarity	NPD8150	Discontinued
0.7237	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2654	Approved
0.723	Intermediate Similarity	NPD1610	Phase 2
0.723	Intermediate Similarity	NPD1611	Approved
0.7225	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1019	Discontinued
0.7215	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6002	Phase 3
0.7215	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6004	Phase 3
0.7215	Intermediate Similarity	NPD6005	Phase 3
0.7213	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD8032	Phase 2
0.7198	Intermediate Similarity	NPD4363	Phase 3
0.7198	Intermediate Similarity	NPD4360	Phase 2
0.7192	Intermediate Similarity	NPD1548	Phase 1
0.7189	Intermediate Similarity	NPD6776	Approved
0.7189	Intermediate Similarity	NPD6781	Approved
0.7189	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6782	Approved
0.7189	Intermediate Similarity	NPD6780	Approved
0.7189	Intermediate Similarity	NPD6777	Approved
0.7189	Intermediate Similarity	NPD6778	Approved
0.7189	Intermediate Similarity	NPD6779	Approved
0.7181	Intermediate Similarity	NPD3972	Approved
0.716	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD8151	Discontinued
0.7158	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4361	Phase 2

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