NPASS Compound

Structure

CID126101 OpenBabel06191715482D 26 28 0 0 1 0 0 0 0 0999 V2000 3.3979 -0.0244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7306 3.1088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9804 6.6194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7006 5.9714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6794 -1.0161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0267 4.5492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3264 3.6279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5178 1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0790 4.7503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5180 0.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5179 1.4534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6786 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5177 0.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6784 2.9076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6787 1.9388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6790 1.9381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8391 0.4843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8392 1.4541 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8393 1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8394 0.4846 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7793 5.6717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6791 0.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6793 2.9381 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1685 5.8728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5453 -0.4993 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 13 1 0 0 0 0 2 14 2 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 6 7 1 0 0 0 0 6 9 2 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 17 2 0 0 0 0 15 14 1 1 0 0 0 15 18 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 6 0 0 0 18 20 1 0 0 0 0 20 22 1 6 0 0 0 20 26 1 0 0 0 0 21 24 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:	358.21
Volume:	385.377
LogP:	3.742
LogD:	3.034
LogS:	-3.667
# Rotatable Bonds:	4
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.712
Synthetic Accessibility Score:	4.619
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.567
MDCK Permeability:	1.675240673648659e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.705
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.307
Plasma Protein Binding (PPB):	88.90225982666016%
Volume Distribution (VD):	0.881
Pgp-substrate:	4.158329486846924%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.186
CYP2C19-inhibitor:	0.115
CYP2C19-substrate:	0.731
CYP2C9-inhibitor:	0.303
CYP2C9-substrate:	0.82
CYP2D6-inhibitor:	0.431
CYP2D6-substrate:	0.519
CYP3A4-inhibitor:	0.874
CYP3A4-substrate:	0.372

ADMET: Excretion

Clearance (CL):	7.438
Half-life (T1/2):	0.608

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.259
Drug-inuced Liver Injury (DILI):	0.194
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.2
Maximum Recommended Daily Dose:	0.866
Skin Sensitization:	0.062
Carcinogencity:	0.164
Eye Corrosion:	0.005
Eye Irritation:	0.109
Respiratory Toxicity:	0.034

Download Data

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

Natural Product: NPC126101

Natural Product ID:	NPC126101
*Common Name:**	Ferruginene B
IUPAC Name:	(5aS,6S,9R,9aR)-9-[(4E)-6-hydroxy-6-methylhepta-1,4-dien-2-yl]-3,6-dimethyl-7,8,9,9a-tetrahydro-5aH-dibenzofuran-1,6-diol
Synonyms:	Ferruginene B
Standard InCHIKey:	ZOCFYPAYCMVCQS-QOACGZPJSA-N
Standard InCHI:	InChI=1S/C22H30O4/c1-13-11-16(23)19-17(12-13)26-20-18(19)15(8-10-22(20,5)25)14(2)7-6-9-21(3,4)24/h6,9,11-12,15,18,20,23-25H,2,7-8,10H2,1,3-5H3/b9-6+/t15-,18+,20-,22-/m0/s1
SMILES:	Cc1cc(c2c(c1)O[C@H]1[C@@H]2[C@@H](CC[C@]1(C)O)C(=C)C/C=C/C(C)(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1775032
PubChem CID:	52951887
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO18212	Rhododendron ferrugineum	Species	Ericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21443171]
NPO18212	Rhododendron ferrugineum	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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	20000.0	nM	PMID[504341]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20000.0	nM	PMID[504341]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20000.0	nM	PMID[504341]

☑ 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 NPC126101 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	407
0.1-0.2	1371
0.2-0.3	3379
0.3-0.4	8449
0.4-0.5	10301
0.5-0.6	3917
0.6-0.7	8651
0.7-0.8	5123
0.8-0.85	860
0.85-0.9	230
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9846	High Similarity	NPC327735
0.9398	High Similarity	NPC472800
0.9137	High Similarity	NPC469557
0.913	High Similarity	NPC477616
0.9124	High Similarity	NPC263261
0.9124	High Similarity	NPC87725
0.9104	High Similarity	NPC124085
0.9104	High Similarity	NPC117048
0.9098	High Similarity	NPC472798
0.9051	High Similarity	NPC254759
0.9051	High Similarity	NPC309124
0.9051	High Similarity	NPC184797
0.9051	High Similarity	NPC160283
0.9044	High Similarity	NPC477938
0.9044	High Similarity	NPC474687
0.903	High Similarity	NPC85435
0.9023	High Similarity	NPC162801
0.9015	High Similarity	NPC472797
0.9	High Similarity	NPC221318
0.8993	High Similarity	NPC258083
0.8986	High Similarity	NPC265075
0.8978	High Similarity	NPC236306
0.8978	High Similarity	NPC292882
0.8978	High Similarity	NPC475836
0.8978	High Similarity	NPC473739
0.8978	High Similarity	NPC232164
0.8971	High Similarity	NPC3049
0.8971	High Similarity	NPC18189
0.8971	High Similarity	NPC262585
0.8971	High Similarity	NPC20829
0.8958	High Similarity	NPC160196
0.8955	High Similarity	NPC13005
0.8936	High Similarity	NPC233980
0.8929	High Similarity	NPC45257
0.8929	High Similarity	NPC12641
0.8929	High Similarity	NPC93323
0.8929	High Similarity	NPC280092
0.8921	High Similarity	NPC107161
0.8913	High Similarity	NPC27495
0.8897	High Similarity	NPC151224
0.8897	High Similarity	NPC134968
0.8889	High Similarity	NPC158331
0.8881	High Similarity	NPC164574
0.8881	High Similarity	NPC268917
0.8881	High Similarity	NPC280653
0.8881	High Similarity	NPC300875
0.8881	High Similarity	NPC129784
0.8881	High Similarity	NPC236014
0.8881	High Similarity	NPC228369
0.8881	High Similarity	NPC12875
0.8881	High Similarity	NPC17343
0.8881	High Similarity	NPC476166
0.8881	High Similarity	NPC206224
0.8881	High Similarity	NPC207892
0.8881	High Similarity	NPC472590
0.8881	High Similarity	NPC196765
0.8881	High Similarity	NPC150011
0.8881	High Similarity	NPC129106
0.8881	High Similarity	NPC118114
0.8873	High Similarity	NPC474397
0.8873	High Similarity	NPC16269
0.8873	High Similarity	NPC21776
0.8872	High Similarity	NPC472795
0.8872	High Similarity	NPC472796
0.8864	High Similarity	NPC469386
0.8857	High Similarity	NPC47633
0.8857	High Similarity	NPC474104
0.8857	High Similarity	NPC102044
0.8857	High Similarity	NPC85264
0.8855	High Similarity	NPC131397
0.8855	High Similarity	NPC476254
0.8849	High Similarity	NPC247291
0.8849	High Similarity	NPC311530
0.8841	High Similarity	NPC32630
0.8841	High Similarity	NPC260741
0.8841	High Similarity	NPC70682
0.8836	High Similarity	NPC188578
0.8836	High Similarity	NPC80918
0.8832	High Similarity	NPC263367
0.8832	High Similarity	NPC162659
0.8832	High Similarity	NPC177160
0.8832	High Similarity	NPC227503
0.8832	High Similarity	NPC234952
0.8832	High Similarity	NPC474639
0.8832	High Similarity	NPC209985
0.8832	High Similarity	NPC10737
0.8832	High Similarity	NPC265433
0.8832	High Similarity	NPC477939
0.8832	High Similarity	NPC54743
0.8832	High Similarity	NPC230734
0.8832	High Similarity	NPC29799
0.8832	High Similarity	NPC248727
0.8832	High Similarity	NPC141717
0.8832	High Similarity	NPC270456
0.8832	High Similarity	NPC156502
0.8824	High Similarity	NPC296915
0.8824	High Similarity	NPC223008
0.8824	High Similarity	NPC49603
0.8824	High Similarity	NPC198154
0.8824	High Similarity	NPC97834
0.8824	High Similarity	NPC287745
0.8824	High Similarity	NPC115335
0.8824	High Similarity	NPC225696
0.8824	High Similarity	NPC193026
0.8824	High Similarity	NPC187616
0.8824	High Similarity	NPC16485
0.8819	High Similarity	NPC158784
0.8815	High Similarity	NPC175067
0.8815	High Similarity	NPC204215
0.8806	High Similarity	NPC470225
0.8806	High Similarity	NPC470727
0.8806	High Similarity	NPC27187
0.8803	High Similarity	NPC260397
0.8797	High Similarity	NPC38604
0.8797	High Similarity	NPC211179
0.8797	High Similarity	NPC47283
0.8797	High Similarity	NPC39064
0.8797	High Similarity	NPC87224
0.8797	High Similarity	NPC222572
0.8794	High Similarity	NPC473108
0.8794	High Similarity	NPC63879
0.8794	High Similarity	NPC469795
0.8794	High Similarity	NPC473845
0.8786	High Similarity	NPC204347
0.8786	High Similarity	NPC59841
0.8786	High Similarity	NPC475891
0.8786	High Similarity	NPC2613
0.8759	High Similarity	NPC61946
0.8759	High Similarity	NPC164787
0.8759	High Similarity	NPC2745
0.8759	High Similarity	NPC470356
0.8759	High Similarity	NPC94750
0.8759	High Similarity	NPC126409
0.8759	High Similarity	NPC112246
0.8759	High Similarity	NPC302915
0.8759	High Similarity	NPC99572
0.8759	High Similarity	NPC473413
0.8759	High Similarity	NPC112939
0.8759	High Similarity	NPC121812
0.8759	High Similarity	NPC474206
0.875	High Similarity	NPC11060
0.875	High Similarity	NPC26394
0.875	High Similarity	NPC469610
0.875	High Similarity	NPC92805
0.875	High Similarity	NPC475840
0.8741	High Similarity	NPC181497
0.8741	High Similarity	NPC101376
0.8741	High Similarity	NPC271945
0.8741	High Similarity	NPC103799
0.8732	High Similarity	NPC472457
0.8732	High Similarity	NPC180953
0.8732	High Similarity	NPC90645
0.8732	High Similarity	NPC181615
0.8731	High Similarity	NPC222108
0.8731	High Similarity	NPC96719
0.8723	High Similarity	NPC173203
0.8723	High Similarity	NPC163508
0.8723	High Similarity	NPC81638
0.8714	High Similarity	NPC35216
0.8714	High Similarity	NPC471389
0.8714	High Similarity	NPC71046
0.8705	High Similarity	NPC471388
0.8705	High Similarity	NPC25966
0.8705	High Similarity	NPC127218
0.8705	High Similarity	NPC245207
0.8705	High Similarity	NPC184613
0.8705	High Similarity	NPC319647
0.8699	High Similarity	NPC325860
0.8699	High Similarity	NPC157783
0.8696	High Similarity	NPC173660
0.8696	High Similarity	NPC306441
0.8696	High Similarity	NPC472336
0.8696	High Similarity	NPC472334
0.8696	High Similarity	NPC476698
0.8696	High Similarity	NPC302701
0.8696	High Similarity	NPC470802
0.8696	High Similarity	NPC16435
0.8696	High Similarity	NPC269091
0.869	High Similarity	NPC195561
0.8686	High Similarity	NPC317380
0.8686	High Similarity	NPC244983
0.8686	High Similarity	NPC326095
0.8686	High Similarity	NPC473107
0.8681	High Similarity	NPC473408
0.8681	High Similarity	NPC212142
0.8676	High Similarity	NPC230219
0.8676	High Similarity	NPC18842
0.8676	High Similarity	NPC469611
0.8671	High Similarity	NPC324492
0.8671	High Similarity	NPC211758
0.8671	High Similarity	NPC317053
0.8671	High Similarity	NPC87794
0.8667	High Similarity	NPC11089
0.8662	High Similarity	NPC15659
0.8662	High Similarity	NPC50250
0.8662	High Similarity	NPC304894
0.8657	High Similarity	NPC53986
0.8657	High Similarity	NPC38664
0.8652	High Similarity	NPC41782
0.8647	High Similarity	NPC262573

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 NPC126101 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	815
0.2-0.3	1751
0.3-0.4	2677
0.4-0.5	1807
0.5-0.6	983
0.6-0.7	629
0.7-0.8	142
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8593	High Similarity	NPD4625	Phase 3
0.8561	High Similarity	NPD4749	Approved
0.854	High Similarity	NPD1612	Clinical (unspecified phase)
0.854	High Similarity	NPD1613	Approved
0.8529	High Similarity	NPD6410	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD3027	Phase 3
0.8394	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD4908	Phase 1
0.8382	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD1610	Phase 2
0.8235	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD2861	Phase 2
0.8088	Intermediate Similarity	NPD6696	Suspended
0.8069	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD4060	Phase 1
0.7986	Intermediate Similarity	NPD6099	Approved
0.7986	Intermediate Similarity	NPD6100	Approved
0.797	Intermediate Similarity	NPD1548	Phase 1
0.7931	Intermediate Similarity	NPD5763	Approved
0.7931	Intermediate Similarity	NPD5762	Approved
0.7885	Intermediate Similarity	NPD6234	Discontinued
0.7823	Intermediate Similarity	NPD6674	Discontinued
0.7792	Intermediate Similarity	NPD37	Approved
0.777	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD4966	Approved
0.7756	Intermediate Similarity	NPD4965	Approved
0.7756	Intermediate Similarity	NPD4967	Phase 2
0.7744	Intermediate Similarity	NPD6671	Approved
0.7742	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD1091	Approved
0.7708	Intermediate Similarity	NPD5735	Approved
0.7692	Intermediate Similarity	NPD4750	Phase 3
0.7677	Intermediate Similarity	NPD1934	Approved
0.7651	Intermediate Similarity	NPD3892	Phase 2
0.7639	Intermediate Similarity	NPD3620	Phase 2
0.7639	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD2238	Phase 2
0.7626	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2677	Approved
0.7586	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5124	Phase 1
0.7571	Intermediate Similarity	NPD8651	Approved
0.7562	Intermediate Similarity	NPD7199	Phase 2
0.7556	Intermediate Similarity	NPD7340	Approved
0.7546	Intermediate Similarity	NPD7228	Approved
0.7538	Intermediate Similarity	NPD290	Approved
0.7535	Intermediate Similarity	NPD3018	Phase 2
0.7532	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD5327	Phase 3
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD422	Phase 1
0.7482	Intermediate Similarity	NPD3705	Approved
0.7481	Intermediate Similarity	NPD7157	Approved
0.7481	Intermediate Similarity	NPD2684	Approved
0.747	Intermediate Similarity	NPD6559	Discontinued
0.7469	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD6355	Discontinued
0.7463	Intermediate Similarity	NPD5283	Phase 1
0.7463	Intermediate Similarity	NPD1398	Phase 1
0.7451	Intermediate Similarity	NPD2533	Approved
0.7451	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2534	Approved
0.7451	Intermediate Similarity	NPD2532	Approved
0.7434	Intermediate Similarity	NPD5058	Phase 3
0.7432	Intermediate Similarity	NPD5588	Approved
0.7421	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1653	Approved
0.7415	Intermediate Similarity	NPD6353	Approved
0.7415	Intermediate Similarity	NPD4097	Suspended
0.7405	Intermediate Similarity	NPD2801	Approved
0.74	Intermediate Similarity	NPD2424	Discontinued
0.7397	Intermediate Similarity	NPD4140	Approved
0.7394	Intermediate Similarity	NPD3094	Phase 2
0.7391	Intermediate Similarity	NPD5494	Approved
0.7388	Intermediate Similarity	NPD7843	Approved
0.7376	Intermediate Similarity	NPD2983	Phase 2
0.7376	Intermediate Similarity	NPD2982	Phase 2
0.7365	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4538	Approved
0.7365	Intermediate Similarity	NPD4536	Approved
0.7351	Intermediate Similarity	NPD1652	Phase 2
0.7346	Intermediate Similarity	NPD6959	Discontinued
0.7338	Intermediate Similarity	NPD5125	Phase 3
0.7338	Intermediate Similarity	NPD5126	Approved
0.7338	Intermediate Similarity	NPD4626	Approved
0.7338	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6005	Phase 3
0.7333	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6004	Phase 3
0.7333	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6002	Phase 3
0.7333	Intermediate Similarity	NPD3818	Discontinued
0.7325	Intermediate Similarity	NPD4380	Phase 2
0.7317	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6166	Phase 2
0.7313	Intermediate Similarity	NPD228	Approved
0.7305	Intermediate Similarity	NPD2232	Approved
0.7305	Intermediate Similarity	NPD2233	Approved
0.7305	Intermediate Similarity	NPD2981	Phase 2
0.7305	Intermediate Similarity	NPD2230	Approved
0.7303	Intermediate Similarity	NPD4628	Phase 3
0.7303	Intermediate Similarity	NPD7466	Approved
0.7301	Intermediate Similarity	NPD6232	Discontinued
0.7301	Intermediate Similarity	NPD7229	Phase 3
0.7297	Intermediate Similarity	NPD6653	Approved
0.7296	Intermediate Similarity	NPD5929	Approved
0.729	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4577	Approved
0.7278	Intermediate Similarity	NPD7313	Approved
0.7278	Intermediate Similarity	NPD7310	Approved
0.7278	Intermediate Similarity	NPD7312	Approved
0.7278	Intermediate Similarity	NPD4578	Approved
0.7278	Intermediate Similarity	NPD7311	Approved
0.7273	Intermediate Similarity	NPD7473	Discontinued
0.7273	Intermediate Similarity	NPD7213	Phase 3
0.7273	Intermediate Similarity	NPD7212	Phase 2
0.7273	Intermediate Similarity	NPD1511	Approved
0.7267	Intermediate Similarity	NPD7075	Discontinued
0.7266	Intermediate Similarity	NPD5691	Approved
0.726	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2969	Approved
0.7256	Intermediate Similarity	NPD2970	Approved
0.7251	Intermediate Similarity	NPD4663	Approved
0.725	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7309	Approved
0.7234	Intermediate Similarity	NPD1611	Approved
0.7234	Intermediate Similarity	NPD3092	Approved
0.7226	Intermediate Similarity	NPD7447	Phase 1
0.7222	Intermediate Similarity	NPD4624	Approved
0.7219	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6599	Discontinued
0.7214	Intermediate Similarity	NPD1778	Approved
0.7212	Intermediate Similarity	NPD2489	Approved
0.7212	Intermediate Similarity	NPD27	Approved
0.7209	Intermediate Similarity	NPD7906	Approved
0.72	Intermediate Similarity	NPD7033	Discontinued
0.72	Intermediate Similarity	NPD5960	Phase 3
0.7197	Intermediate Similarity	NPD968	Approved
0.7195	Intermediate Similarity	NPD3051	Approved
0.7195	Intermediate Similarity	NPD3787	Discontinued
0.7192	Intermediate Similarity	NPD7095	Approved
0.719	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4110	Phase 3
0.719	Intermediate Similarity	NPD3750	Approved
0.7188	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7819	Suspended
0.7183	Intermediate Similarity	NPD2231	Phase 2
0.7183	Intermediate Similarity	NPD2235	Phase 2
0.7181	Intermediate Similarity	NPD2157	Approved
0.7179	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1512	Approved
0.7178	Intermediate Similarity	NPD4666	Phase 3
0.7172	Intermediate Similarity	NPD1712	Approved
0.7171	Intermediate Similarity	NPD1549	Phase 2
0.7171	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7037	Approved
0.717	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6072	Discontinued
0.7164	Intermediate Similarity	NPD3021	Approved
0.7164	Intermediate Similarity	NPD3022	Approved
0.7163	Intermediate Similarity	NPD3496	Discontinued
0.716	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7240	Approved
0.7154	Intermediate Similarity	NPD846	Approved
0.7154	Intermediate Similarity	NPD940	Approved
0.7152	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD2563	Approved
0.7143	Intermediate Similarity	NPD7074	Phase 3
0.7143	Intermediate Similarity	NPD7985	Registered
0.7143	Intermediate Similarity	NPD3817	Phase 2
0.7143	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2560	Approved
0.7143	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7133	Intermediate Similarity	NPD7097	Phase 1
0.7132	Intermediate Similarity	NPD7635	Approved
0.7117	Intermediate Similarity	NPD5709	Phase 3
0.7115	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4678	Approved
0.7107	Intermediate Similarity	NPD4675	Approved
0.7105	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1375	Discontinued
0.7103	Intermediate Similarity	NPD6584	Phase 3
0.7093	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7054	Approved
0.7078	Intermediate Similarity	NPD6331	Phase 2
0.7078	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3091	Approved
0.7071	Intermediate Similarity	NPD7741	Discontinued
0.707	Intermediate Similarity	NPD6090	Discontinued
0.707	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1607	Approved
0.7063	Intermediate Similarity	NPD1608	Approved
0.7051	Intermediate Similarity	NPD6799	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