NPASS Compound

Structure

CID280833 OpenBabel06191716092D 28 30 0 0 1 0 0 0 0 0999 V2000 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 3.4641 1.0000 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 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 7 27 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 15 2 0 0 0 0 12 16 1 0 0 0 0 13 24 2 0 0 0 0 13 28 1 0 0 0 0 14 17 1 0 0 0 0 14 28 1 6 0 0 0 15 22 1 0 0 0 0 15 23 1 0 0 0 0 16 19 1 0 0 0 0 16 21 2 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 18 23 1 0 0 0 0 19 25 2 0 0 0 0 20 21 1 0 0 0 0 20 26 2 0 0 0 0 21 27 1 0 0 0 0 23 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.21
Volume:	408.827
LogP:	4.781
LogD:	2.914
LogS:	-3.756
# Rotatable Bonds:	4
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.427
Synthetic Accessibility Score:	4.356
Fsp3:	0.522
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.792
MDCK Permeability:	2.0193254385958426e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.07
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	92.3311996459961%
Volume Distribution (VD):	2.308
Pgp-substrate:	9.814668655395508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.134
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.361
CYP2C19-substrate:	0.877
CYP2C9-inhibitor:	0.85
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.073
CYP2D6-substrate:	0.188
CYP3A4-inhibitor:	0.436
CYP3A4-substrate:	0.761

ADMET: Excretion

Clearance (CL):	1.654
Half-life (T1/2):	0.128

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.386
Drug-inuced Liver Injury (DILI):	0.441
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.876
Maximum Recommended Daily Dose:	0.305
Skin Sensitization:	0.192
Carcinogencity:	0.094
Eye Corrosion:	0.003
Eye Irritation:	0.555
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC280833

Natural Product ID:	NPC280833
*Common Name:**	7-Acetyl-12-Methoxy-11,14-Dioxoabieta-5,8,12-Triene
IUPAC Name:	[(4aS,9R)-6-methoxy-1,1,4a-trimethyl-5,8-dioxo-7-propan-2-yl-2,3,4,9-tetrahydrophenanthren-9-yl] acetate
Synonyms:	12-methyl-5-dehydroacetylhorminone
Standard InCHIKey:	KRHKKRFFQDNBIN-FATZIPQQSA-N
Standard InCHI:	InChI=1S/C23H30O5/c1-12(2)16-19(25)17-14(28-13(3)24)11-15-22(4,5)9-8-10-23(15,6)18(17)20(26)21(16)27-7/h11-12,14H,8-10H2,1-7H3/t14-,23+/m1/s1
SMILES:	CC(C)C1=C(C(=O)C2=C([C@@H](C=C3C(C)(C)CCC[C@]23C)OC(=O)C)C1=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457940
PubChem CID:	467787
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO29303	Salvia multicaulis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9428161]
NPO29303	Salvia multicaulis	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[9428161]
NPO29303	Salvia multicaulis	Species	Lamiaceae	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
MIC	2
Others	1

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	0.89	ug.mL-1	PMID[528122]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	7.2	ug.mL-1	PMID[528122]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	>	7.0	mm	PMID[528122]

☑ 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 NPC280833 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	224
0.1-0.2	1354
0.2-0.3	4787
0.3-0.4	9882
0.4-0.5	14332
0.5-0.6	7192
0.6-0.7	4242
0.7-0.8	660
0.8-0.85	19
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8778	High Similarity	NPC271652
0.875	High Similarity	NPC53454
0.8353	Intermediate Similarity	NPC150646
0.8352	Intermediate Similarity	NPC113393
0.8333	Intermediate Similarity	NPC307298
0.8295	Intermediate Similarity	NPC474359
0.8202	Intermediate Similarity	NPC90287
0.8182	Intermediate Similarity	NPC222358
0.8111	Intermediate Similarity	NPC220478
0.8085	Intermediate Similarity	NPC470697
0.8085	Intermediate Similarity	NPC148463
0.8065	Intermediate Similarity	NPC166110
0.8061	Intermediate Similarity	NPC80781
0.8	Intermediate Similarity	NPC133652
0.8	Intermediate Similarity	NPC189311
0.8	Intermediate Similarity	NPC295347
0.7979	Intermediate Similarity	NPC476598
0.7979	Intermediate Similarity	NPC248193
0.7979	Intermediate Similarity	NPC476597
0.7978	Intermediate Similarity	NPC193198
0.7957	Intermediate Similarity	NPC469372
0.7957	Intermediate Similarity	NPC212679
0.7957	Intermediate Similarity	NPC220454
0.7957	Intermediate Similarity	NPC469595
0.7957	Intermediate Similarity	NPC8062
0.7955	Intermediate Similarity	NPC282293
0.7955	Intermediate Similarity	NPC474085
0.7938	Intermediate Similarity	NPC264378
0.7935	Intermediate Similarity	NPC143025
0.7935	Intermediate Similarity	NPC472302
0.7895	Intermediate Similarity	NPC476596
0.7895	Intermediate Similarity	NPC84893
0.7857	Intermediate Similarity	NPC54705
0.7849	Intermediate Similarity	NPC142159
0.7849	Intermediate Similarity	NPC284561
0.7849	Intermediate Similarity	NPC95364
0.7835	Intermediate Similarity	NPC208094
0.7826	Intermediate Similarity	NPC272039
0.7826	Intermediate Similarity	NPC220930
0.7826	Intermediate Similarity	NPC478144
0.7802	Intermediate Similarity	NPC263997
0.7802	Intermediate Similarity	NPC8518
0.7802	Intermediate Similarity	NPC132228
0.7802	Intermediate Similarity	NPC474680
0.7778	Intermediate Similarity	NPC288281
0.7778	Intermediate Similarity	NPC472643
0.7778	Intermediate Similarity	NPC471699
0.7778	Intermediate Similarity	NPC258985
0.7766	Intermediate Similarity	NPC51486
0.7766	Intermediate Similarity	NPC471818
0.7753	Intermediate Similarity	NPC475833
0.7742	Intermediate Similarity	NPC226863
0.7717	Intermediate Similarity	NPC279859
0.7717	Intermediate Similarity	NPC261721
0.7717	Intermediate Similarity	NPC38576
0.7708	Intermediate Similarity	NPC53685
0.7708	Intermediate Similarity	NPC38830
0.7701	Intermediate Similarity	NPC283087
0.7692	Intermediate Similarity	NPC60951
0.7684	Intermediate Similarity	NPC193396
0.7684	Intermediate Similarity	NPC32944
0.7677	Intermediate Similarity	NPC476299
0.7677	Intermediate Similarity	NPC476933
0.7677	Intermediate Similarity	NPC104861
0.7677	Intermediate Similarity	NPC474012
0.7667	Intermediate Similarity	NPC200513
0.7667	Intermediate Similarity	NPC178676
0.766	Intermediate Similarity	NPC5509
0.7653	Intermediate Similarity	NPC53844
0.7653	Intermediate Similarity	NPC84335
0.7653	Intermediate Similarity	NPC38530
0.7634	Intermediate Similarity	NPC477228
0.7634	Intermediate Similarity	NPC478145
0.7634	Intermediate Similarity	NPC125925
0.7629	Intermediate Similarity	NPC209355
0.7629	Intermediate Similarity	NPC777
0.7624	Intermediate Similarity	NPC271059
0.7624	Intermediate Similarity	NPC25666
0.7614	Intermediate Similarity	NPC471220
0.7609	Intermediate Similarity	NPC110405
0.7609	Intermediate Similarity	NPC6185
0.7609	Intermediate Similarity	NPC177932
0.7609	Intermediate Similarity	NPC96621
0.7609	Intermediate Similarity	NPC241512
0.7604	Intermediate Similarity	NPC115021
0.7604	Intermediate Similarity	NPC475657
0.76	Intermediate Similarity	NPC469657
0.76	Intermediate Similarity	NPC93744
0.76	Intermediate Similarity	NPC476888
0.76	Intermediate Similarity	NPC244456
0.7586	Intermediate Similarity	NPC40353
0.7582	Intermediate Similarity	NPC22611
0.7582	Intermediate Similarity	NPC105803
0.7582	Intermediate Similarity	NPC474703
0.7579	Intermediate Similarity	NPC213636
0.7579	Intermediate Similarity	NPC161638
0.7579	Intermediate Similarity	NPC253177
0.7579	Intermediate Similarity	NPC280592
0.7576	Intermediate Similarity	NPC316598
0.7573	Intermediate Similarity	NPC91034
0.7553	Intermediate Similarity	NPC469653
0.7553	Intermediate Similarity	NPC475902
0.7553	Intermediate Similarity	NPC478259
0.7553	Intermediate Similarity	NPC475906
0.7553	Intermediate Similarity	NPC215831
0.7553	Intermediate Similarity	NPC24816
0.7553	Intermediate Similarity	NPC478261
0.7553	Intermediate Similarity	NPC469628
0.7553	Intermediate Similarity	NPC478260
0.7553	Intermediate Similarity	NPC471047
0.7553	Intermediate Similarity	NPC469631
0.7553	Intermediate Similarity	NPC477128
0.7551	Intermediate Similarity	NPC184065
0.7551	Intermediate Similarity	NPC112654
0.7528	Intermediate Similarity	NPC471299
0.7527	Intermediate Similarity	NPC472009
0.7527	Intermediate Similarity	NPC202394
0.7526	Intermediate Similarity	NPC477129
0.7526	Intermediate Similarity	NPC477130
0.7526	Intermediate Similarity	NPC476415
0.7525	Intermediate Similarity	NPC40918
0.7525	Intermediate Similarity	NPC476890
0.75	Intermediate Similarity	NPC472814
0.75	Intermediate Similarity	NPC322903
0.75	Intermediate Similarity	NPC177037
0.75	Intermediate Similarity	NPC470036
0.75	Intermediate Similarity	NPC174167
0.75	Intermediate Similarity	NPC45579
0.75	Intermediate Similarity	NPC174314
0.75	Intermediate Similarity	NPC471329
0.75	Intermediate Similarity	NPC472300
0.75	Intermediate Similarity	NPC149869
0.75	Intermediate Similarity	NPC219874
0.75	Intermediate Similarity	NPC120158
0.75	Intermediate Similarity	NPC471225
0.75	Intermediate Similarity	NPC316500
0.75	Intermediate Similarity	NPC473944
0.75	Intermediate Similarity	NPC30486
0.75	Intermediate Similarity	NPC117685
0.75	Intermediate Similarity	NPC472644
0.75	Intermediate Similarity	NPC296114
0.75	Intermediate Similarity	NPC475193
0.7477	Intermediate Similarity	NPC159333
0.7475	Intermediate Similarity	NPC69385
0.7475	Intermediate Similarity	NPC2049
0.7475	Intermediate Similarity	NPC478233
0.7474	Intermediate Similarity	NPC177141
0.7474	Intermediate Similarity	NPC173042
0.7474	Intermediate Similarity	NPC50070
0.7474	Intermediate Similarity	NPC73995
0.7473	Intermediate Similarity	NPC103486
0.7453	Intermediate Similarity	NPC324683
0.7451	Intermediate Similarity	NPC470954
0.7451	Intermediate Similarity	NPC320154
0.7451	Intermediate Similarity	NPC476889
0.7449	Intermediate Similarity	NPC474490
0.7449	Intermediate Similarity	NPC31021
0.7449	Intermediate Similarity	NPC470978
0.7449	Intermediate Similarity	NPC470974
0.7449	Intermediate Similarity	NPC33473
0.7447	Intermediate Similarity	NPC38885
0.7447	Intermediate Similarity	NPC312561
0.7447	Intermediate Similarity	NPC471739
0.7447	Intermediate Similarity	NPC472007
0.7444	Intermediate Similarity	NPC304795
0.7444	Intermediate Similarity	NPC195424
0.7444	Intermediate Similarity	NPC474956
0.7426	Intermediate Similarity	NPC469851
0.7426	Intermediate Similarity	NPC476478
0.7426	Intermediate Similarity	NPC194028
0.7426	Intermediate Similarity	NPC323441
0.7426	Intermediate Similarity	NPC473384
0.7426	Intermediate Similarity	NPC310981
0.7426	Intermediate Similarity	NPC168319
0.7423	Intermediate Similarity	NPC169343
0.7423	Intermediate Similarity	NPC263780
0.7419	Intermediate Similarity	NPC323765
0.7419	Intermediate Similarity	NPC476678
0.7419	Intermediate Similarity	NPC65661
0.7419	Intermediate Similarity	NPC32037
0.7416	Intermediate Similarity	NPC23778
0.7416	Intermediate Similarity	NPC478247
0.7416	Intermediate Similarity	NPC478246
0.7404	Intermediate Similarity	NPC475294
0.74	Intermediate Similarity	NPC222011
0.74	Intermediate Similarity	NPC54843
0.74	Intermediate Similarity	NPC176845
0.74	Intermediate Similarity	NPC478056
0.7396	Intermediate Similarity	NPC159748
0.7396	Intermediate Similarity	NPC198818
0.7396	Intermediate Similarity	NPC223093
0.7396	Intermediate Similarity	NPC476369
0.7396	Intermediate Similarity	NPC101651
0.7396	Intermediate Similarity	NPC476437
0.7396	Intermediate Similarity	NPC145666
0.7396	Intermediate Similarity	NPC232426
0.7396	Intermediate Similarity	NPC474209
0.7396	Intermediate Similarity	NPC475823
0.7396	Intermediate Similarity	NPC281942
0.7396	Intermediate Similarity	NPC152467

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 NPC280833 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1676
0.2-0.3	3702
0.3-0.4	2335
0.4-0.5	863
0.5-0.6	236
0.6-0.7	117
0.7-0.8	23
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7742	Intermediate Similarity	NPD6672	Approved
0.7742	Intermediate Similarity	NPD5737	Approved
0.7684	Intermediate Similarity	NPD5693	Phase 1
0.7667	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD1694	Approved
0.7449	Intermediate Similarity	NPD5695	Phase 3
0.7396	Intermediate Similarity	NPD5692	Phase 3
0.734	Intermediate Similarity	NPD7521	Approved
0.734	Intermediate Similarity	NPD6409	Approved
0.734	Intermediate Similarity	NPD6684	Approved
0.734	Intermediate Similarity	NPD5330	Approved
0.734	Intermediate Similarity	NPD7146	Approved
0.734	Intermediate Similarity	NPD7334	Approved
0.732	Intermediate Similarity	NPD6050	Approved
0.732	Intermediate Similarity	NPD5694	Approved
0.7292	Intermediate Similarity	NPD6904	Approved
0.7292	Intermediate Similarity	NPD6080	Approved
0.7292	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6673	Approved
0.7253	Intermediate Similarity	NPD4695	Discontinued
0.7188	Intermediate Similarity	NPD6903	Approved
0.7188	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6084	Phase 2
0.7129	Intermediate Similarity	NPD6083	Phase 2
0.71	Intermediate Similarity	NPD5654	Approved
0.7059	Intermediate Similarity	NPD5696	Approved
0.7	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7900	Approved
0.7	Intermediate Similarity	NPD7748	Approved
0.6979	Remote Similarity	NPD6098	Approved
0.6979	Remote Similarity	NPD5279	Phase 3
0.697	Remote Similarity	NPD6411	Approved
0.6961	Remote Similarity	NPD5959	Approved
0.6923	Remote Similarity	NPD4756	Discovery
0.6915	Remote Similarity	NPD5209	Approved
0.69	Remote Similarity	NPD6399	Phase 3
0.6893	Remote Similarity	NPD4225	Approved
0.6889	Remote Similarity	NPD8039	Approved
0.6869	Remote Similarity	NPD5785	Approved
0.6832	Remote Similarity	NPD5282	Discontinued
0.6822	Remote Similarity	NPD6675	Approved
0.6822	Remote Similarity	NPD7128	Approved
0.6822	Remote Similarity	NPD5739	Approved
0.6822	Remote Similarity	NPD6402	Approved
0.6814	Remote Similarity	NPD7115	Discovery
0.68	Remote Similarity	NPD7515	Phase 2
0.6796	Remote Similarity	NPD7902	Approved
0.6768	Remote Similarity	NPD6101	Approved
0.6768	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5697	Approved
0.6759	Remote Similarity	NPD5701	Approved
0.6735	Remote Similarity	NPD3573	Approved
0.6733	Remote Similarity	NPD5779	Approved
0.6733	Remote Similarity	NPD5778	Approved
0.6731	Remote Similarity	NPD7638	Approved
0.67	Remote Similarity	NPD5207	Approved
0.6697	Remote Similarity	NPD7320	Approved
0.6697	Remote Similarity	NPD6899	Approved
0.6697	Remote Similarity	NPD6881	Approved
0.6697	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6636	Remote Similarity	NPD6012	Approved
0.6636	Remote Similarity	NPD6372	Approved
0.6636	Remote Similarity	NPD6013	Approved
0.6636	Remote Similarity	NPD6373	Approved
0.6636	Remote Similarity	NPD6014	Approved
0.6602	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6051	Approved
0.66	Remote Similarity	NPD4753	Phase 2
0.6598	Remote Similarity	NPD3666	Approved
0.6598	Remote Similarity	NPD3665	Phase 1
0.6598	Remote Similarity	NPD3668	Phase 3
0.6598	Remote Similarity	NPD3133	Approved
0.6577	Remote Similarity	NPD7102	Approved
0.6577	Remote Similarity	NPD7290	Approved
0.6577	Remote Similarity	NPD6883	Approved
0.6562	Remote Similarity	NPD3667	Approved
0.6552	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3704	Approved
0.6545	Remote Similarity	NPD6686	Approved
0.6538	Remote Similarity	NPD7732	Phase 3
0.6535	Remote Similarity	NPD46	Approved
0.6535	Remote Similarity	NPD6698	Approved
0.6518	Remote Similarity	NPD6649	Approved
0.6518	Remote Similarity	NPD6869	Approved
0.6518	Remote Similarity	NPD6847	Approved
0.6518	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6650	Approved
0.6518	Remote Similarity	NPD6617	Approved
0.6518	Remote Similarity	NPD8130	Phase 1
0.6514	Remote Similarity	NPD6008	Approved
0.6495	Remote Similarity	NPD7154	Phase 3
0.6471	Remote Similarity	NPD5281	Approved
0.6471	Remote Similarity	NPD5284	Approved
0.6465	Remote Similarity	NPD5280	Approved
0.6465	Remote Similarity	NPD4694	Approved
0.6465	Remote Similarity	NPD3618	Phase 1
0.6465	Remote Similarity	NPD5690	Phase 2
0.6465	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6053	Discontinued
0.646	Remote Similarity	NPD8297	Approved
0.646	Remote Similarity	NPD6882	Approved
0.6455	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4786	Approved
0.6429	Remote Similarity	NPD4197	Approved
0.6381	Remote Similarity	NPD5222	Approved
0.6381	Remote Similarity	NPD5221	Approved
0.6381	Remote Similarity	NPD4697	Phase 3
0.6381	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5363	Approved
0.6364	Remote Similarity	NPD5329	Approved
0.6356	Remote Similarity	NPD6319	Approved
0.6354	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6001	Approved
0.6339	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5173	Approved
0.6321	Remote Similarity	NPD4755	Approved
0.6306	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6614	Approved
0.63	Remote Similarity	NPD4519	Discontinued
0.63	Remote Similarity	NPD4623	Approved
0.6293	Remote Similarity	NPD6274	Approved
0.6293	Remote Similarity	NPD6868	Approved
0.6286	Remote Similarity	NPD5210	Approved
0.6286	Remote Similarity	NPD4629	Approved
0.6283	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6371	Approved
0.6283	Remote Similarity	NPD2067	Discontinued
0.6275	Remote Similarity	NPD5328	Approved
0.6263	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.624	Remote Similarity	NPD7260	Phase 2
0.6239	Remote Similarity	NPD5211	Phase 2
0.6239	Remote Similarity	NPD7632	Discontinued
0.6239	Remote Similarity	NPD6317	Approved
0.6226	Remote Similarity	NPD7614	Phase 1
0.6224	Remote Similarity	NPD4223	Phase 3
0.6224	Remote Similarity	NPD4269	Approved
0.6224	Remote Similarity	NPD4221	Approved
0.6224	Remote Similarity	NPD4270	Approved
0.6207	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5286	Approved
0.6204	Remote Similarity	NPD4700	Approved
0.6204	Remote Similarity	NPD4696	Approved
0.6204	Remote Similarity	NPD5285	Approved
0.6198	Remote Similarity	NPD8328	Phase 3
0.6196	Remote Similarity	NPD5276	Approved
0.6186	Remote Similarity	NPD6314	Approved
0.6186	Remote Similarity	NPD6335	Approved
0.6186	Remote Similarity	NPD6313	Approved
0.6154	Remote Similarity	NPD7637	Suspended
0.6154	Remote Similarity	NPD6079	Approved
0.6154	Remote Similarity	NPD4137	Phase 3
0.6148	Remote Similarity	NPD7492	Approved
0.6147	Remote Similarity	NPD5223	Approved
0.6146	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5786	Approved
0.6134	Remote Similarity	NPD7100	Approved
0.6134	Remote Similarity	NPD7101	Approved
0.6126	Remote Similarity	NPD5141	Approved
0.6122	Remote Similarity	NPD5369	Approved
0.6121	Remote Similarity	NPD4632	Approved
0.6102	Remote Similarity	NPD6009	Approved
0.6098	Remote Similarity	NPD6616	Approved
0.6095	Remote Similarity	NPD4202	Approved
0.6095	Remote Similarity	NPD5133	Approved
0.6091	Remote Similarity	NPD5226	Approved
0.6091	Remote Similarity	NPD5225	Approved
0.6091	Remote Similarity	NPD4633	Approved
0.6091	Remote Similarity	NPD5224	Approved
0.6087	Remote Similarity	NPD4691	Approved
0.6087	Remote Similarity	NPD4747	Approved
0.6083	Remote Similarity	NPD6059	Approved
0.6083	Remote Similarity	NPD6054	Approved
0.6064	Remote Similarity	NPD5733	Approved
0.6064	Remote Similarity	NPD4687	Approved
0.6063	Remote Similarity	NPD6845	Suspended
0.6048	Remote Similarity	NPD7078	Approved
0.6048	Remote Similarity	NPD8293	Discontinued
0.604	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6052	Approved
0.6036	Remote Similarity	NPD5175	Approved
0.6036	Remote Similarity	NPD5174	Approved
0.6036	Remote Similarity	NPD4754	Approved
0.6033	Remote Similarity	NPD6016	Approved
0.6033	Remote Similarity	NPD5983	Phase 2
0.6033	Remote Similarity	NPD6015	Approved
0.6033	Remote Similarity	NPD6909	Approved
0.6033	Remote Similarity	NPD6908	Approved
0.602	Remote Similarity	NPD4252	Approved
0.6018	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD5362	Discontinued
0.6	Remote Similarity	NPD7736	Approved
0.6	Remote Similarity	NPD6110	Phase 1

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