NPASS Compound

Structure

NPC240508 OpenBabel07101718332D 24 28 0 0 1 0 0 0 0 0999 V2000 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 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 9 1 0 0 0 0 4 5 1 0 0 0 0 4 10 1 0 0 0 0 5 19 1 0 0 0 0 6 9 2 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 20 1 0 0 0 0 9 24 1 0 0 0 0 10 20 1 6 0 0 0 11 16 1 0 0 0 0 11 18 2 0 0 0 0 12 14 1 0 0 0 0 12 21 2 0 0 0 0 13 19 1 1 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 16 2 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 2 1 1 0 0 0 20 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.15
Volume:	333.672
LogP:	4.702
LogD:	3.518
LogS:	-4.305
# Rotatable Bonds:	0
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.702
Synthetic Accessibility Score:	4.35
Fsp3:	0.55
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:	-4.766
MDCK Permeability:	1.8366470612818375e-05
Pgp-inhibitor:	0.036
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.294

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089
Plasma Protein Binding (PPB):	93.04920196533203%
Volume Distribution (VD):	0.838
Pgp-substrate:	9.445780754089355%

ADMET: Metabolism

CYP1A2-inhibitor:	0.866
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.176
CYP2C19-substrate:	0.673
CYP2C9-inhibitor:	0.517
CYP2C9-substrate:	0.53
CYP2D6-inhibitor:	0.568
CYP2D6-substrate:	0.31
CYP3A4-inhibitor:	0.396
CYP3A4-substrate:	0.208

ADMET: Excretion

Clearance (CL):	15.655
Half-life (T1/2):	0.238

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.317
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.125
Rat Oral Acute Toxicity:	0.82
Maximum Recommended Daily Dose:	0.846
Skin Sensitization:	0.881
Carcinogencity:	0.858
Eye Corrosion:	0.003
Eye Irritation:	0.379
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC240508

Natural Product ID:	NPC240508
*Common Name:**	YLFXZDORYFPSOA-DLVGZBSQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YLFXZDORYFPSOA-DLVGZBSQSA-N
Standard InCHI:	InChI=1S/C20H22O4/c1-9-6-11-16(22)14-12(21)7-13-19(2,5-4-10-8-20(10,13)3)15(14)17(23)18(11)24-9/h6,10,13,22-23H,4-5,7-8H2,1-3H3/t10-,13+,19-,20+/m0/s1
SMILES:	Cc1cc2c(o1)c(O)c1c(c2O)C(=O)C[C@@H]2[C@]1(C)CC[C@@H]1[C@@]2(C)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1287937
PubChem CID:	52949744
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives

*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
NPO24239	Teucrium polium	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[21084196]
NPO24239	Teucrium polium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24239	Teucrium polium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24239	Teucrium polium	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
IC50	1
Others	1

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	130000.0	nM	PMID[533392]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	50.0	%	PMID[533392]

☑ 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 NPC240508 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	501
0.1-0.2	2029
0.2-0.3	4039
0.3-0.4	10649
0.4-0.5	7816
0.5-0.6	4425
0.6-0.7	5797
0.7-0.8	5849
0.8-0.85	1284
0.85-0.9	292
0.9-0.95	9
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC246153
0.9708	High Similarity	NPC240808
0.9702	High Similarity	NPC23553
0.9702	High Similarity	NPC77179
0.9586	High Similarity	NPC221820
0.9532	High Similarity	NPC228209
0.9419	High Similarity	NPC8927
0.9302	High Similarity	NPC476273
0.9186	High Similarity	NPC8127
0.9186	High Similarity	NPC49667
0.907	High Similarity	NPC476640
0.907	High Similarity	NPC65885
0.907	High Similarity	NPC82217
0.907	High Similarity	NPC216842
0.9059	High Similarity	NPC470704
0.9048	High Similarity	NPC470694
0.9045	High Similarity	NPC295436
0.9034	High Similarity	NPC476170
0.9017	High Similarity	NPC227906
0.9017	High Similarity	NPC287243
0.9012	High Similarity	NPC54098
0.9012	High Similarity	NPC230619
0.8994	High Similarity	NPC270837
0.8994	High Similarity	NPC133065
0.8953	High Similarity	NPC28042
0.8953	High Similarity	NPC476641
0.8947	High Similarity	NPC232936
0.8941	High Similarity	NPC102372
0.8941	High Similarity	NPC39306
0.8935	High Similarity	NPC294965
0.8914	High Similarity	NPC246877
0.8914	High Similarity	NPC297807
0.8908	High Similarity	NPC245975
0.8908	High Similarity	NPC289244
0.8895	High Similarity	NPC213416
0.8895	High Similarity	NPC247136
0.8889	High Similarity	NPC60848
0.8882	High Similarity	NPC236132
0.8882	High Similarity	NPC220313
0.8876	High Similarity	NPC66288
0.887	High Similarity	NPC471842
0.8869	High Similarity	NPC100123
0.8851	High Similarity	NPC30550
0.8851	High Similarity	NPC277510
0.8837	High Similarity	NPC126204
0.8837	High Similarity	NPC95715
0.8837	High Similarity	NPC247973
0.8837	High Similarity	NPC50394
0.883	High Similarity	NPC37183
0.883	High Similarity	NPC25361
0.883	High Similarity	NPC473286
0.883	High Similarity	NPC326520
0.883	High Similarity	NPC36320
0.883	High Similarity	NPC45449
0.8824	High Similarity	NPC84515
0.8824	High Similarity	NPC312056
0.8817	High Similarity	NPC235018
0.8817	High Similarity	NPC84571
0.8817	High Similarity	NPC320359
0.8817	High Similarity	NPC228785
0.8817	High Similarity	NPC14353
0.8817	High Similarity	NPC56085
0.8817	High Similarity	NPC119224
0.8817	High Similarity	NPC45146
0.8814	High Similarity	NPC475996
0.8807	High Similarity	NPC98546
0.8793	High Similarity	NPC158226
0.8793	High Similarity	NPC307286
0.8786	High Similarity	NPC202470
0.8786	High Similarity	NPC165979
0.8786	High Similarity	NPC163130
0.8779	High Similarity	NPC277480
0.8779	High Similarity	NPC170245
0.8779	High Similarity	NPC37870
0.8772	High Similarity	NPC263092
0.8772	High Similarity	NPC208120
0.8772	High Similarity	NPC329669
0.8772	High Similarity	NPC472278
0.8772	High Similarity	NPC473313
0.8772	High Similarity	NPC1706
0.8772	High Similarity	NPC39305
0.8772	High Similarity	NPC59295
0.8772	High Similarity	NPC1755
0.8772	High Similarity	NPC18100
0.8772	High Similarity	NPC173587
0.8772	High Similarity	NPC197168
0.8765	High Similarity	NPC258331
0.8765	High Similarity	NPC40491
0.8765	High Similarity	NPC311740
0.8765	High Similarity	NPC32694
0.8765	High Similarity	NPC188486
0.8765	High Similarity	NPC61010
0.8765	High Similarity	NPC278052
0.8765	High Similarity	NPC472275
0.8757	High Similarity	NPC104682
0.8757	High Similarity	NPC196879
0.8757	High Similarity	NPC235448
0.8757	High Similarity	NPC172770
0.8757	High Similarity	NPC185258
0.875	High Similarity	NPC274730
0.875	High Similarity	NPC471841
0.875	High Similarity	NPC138243
0.875	High Similarity	NPC142339
0.8743	High Similarity	NPC310794
0.8736	High Similarity	NPC109827
0.8736	High Similarity	NPC101107
0.8736	High Similarity	NPC124470
0.8736	High Similarity	NPC131866
0.8728	High Similarity	NPC478060
0.8728	High Similarity	NPC471975
0.8728	High Similarity	NPC470374
0.8728	High Similarity	NPC470377
0.8728	High Similarity	NPC476306
0.8728	High Similarity	NPC478059
0.8721	High Similarity	NPC472277
0.8721	High Similarity	NPC146584
0.8721	High Similarity	NPC21016
0.8715	High Similarity	NPC71260
0.8713	High Similarity	NPC272722
0.8713	High Similarity	NPC81679
0.8713	High Similarity	NPC238995
0.8713	High Similarity	NPC25152
0.8708	High Similarity	NPC47883
0.8706	High Similarity	NPC80375
0.8706	High Similarity	NPC246478
0.8698	High Similarity	NPC262286
0.8698	High Similarity	NPC199463
0.8698	High Similarity	NPC241904
0.8698	High Similarity	NPC300727
0.8698	High Similarity	NPC37543
0.8698	High Similarity	NPC304008
0.8698	High Similarity	NPC187745
0.8698	High Similarity	NPC79053
0.8698	High Similarity	NPC236796
0.8698	High Similarity	NPC165977
0.8698	High Similarity	NPC36852
0.8698	High Similarity	NPC161960
0.8698	High Similarity	NPC217677
0.8686	High Similarity	NPC28589
0.8686	High Similarity	NPC248593
0.8686	High Similarity	NPC174700
0.8678	High Similarity	NPC475805
0.8678	High Similarity	NPC99613
0.8678	High Similarity	NPC476637
0.8678	High Similarity	NPC49487
0.8671	High Similarity	NPC235610
0.8671	High Similarity	NPC29160
0.8663	High Similarity	NPC205265
0.8663	High Similarity	NPC472281
0.8663	High Similarity	NPC475985
0.8663	High Similarity	NPC236521
0.8663	High Similarity	NPC189473
0.8663	High Similarity	NPC306321
0.8663	High Similarity	NPC303460
0.8663	High Similarity	NPC319200
0.8663	High Similarity	NPC187491
0.8663	High Similarity	NPC29055
0.8663	High Similarity	NPC248638
0.8663	High Similarity	NPC207690
0.8663	High Similarity	NPC23298
0.8663	High Similarity	NPC7483
0.8663	High Similarity	NPC475055
0.8663	High Similarity	NPC41301
0.8663	High Similarity	NPC152659
0.8659	High Similarity	NPC182693
0.8655	High Similarity	NPC472906
0.8655	High Similarity	NPC278427
0.8655	High Similarity	NPC187354
0.8647	High Similarity	NPC476242
0.8647	High Similarity	NPC195832
0.8647	High Similarity	NPC16935
0.8647	High Similarity	NPC46736
0.8644	High Similarity	NPC478050
0.8639	High Similarity	NPC45131
0.8639	High Similarity	NPC3980
0.8639	High Similarity	NPC5379
0.8639	High Similarity	NPC68093
0.8639	High Similarity	NPC472461
0.8639	High Similarity	NPC115853
0.8639	High Similarity	NPC14561
0.8639	High Similarity	NPC180924
0.8639	High Similarity	NPC475799
0.8639	High Similarity	NPC13779
0.8639	High Similarity	NPC77807
0.8639	High Similarity	NPC191146
0.8636	High Similarity	NPC473834
0.8636	High Similarity	NPC117450
0.8636	High Similarity	NPC149846
0.8631	High Similarity	NPC89474
0.8631	High Similarity	NPC273248
0.8629	High Similarity	NPC313717
0.8629	High Similarity	NPC218533
0.8629	High Similarity	NPC315306
0.8629	High Similarity	NPC78830
0.8629	High Similarity	NPC472276
0.8621	High Similarity	NPC234331
0.8621	High Similarity	NPC241820
0.8621	High Similarity	NPC150131
0.8613	High Similarity	NPC26386
0.8613	High Similarity	NPC472450

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 NPC240508 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	429
0.1-0.2	1034
0.2-0.3	1879
0.3-0.4	2857
0.4-0.5	1755
0.5-0.6	792
0.6-0.7	278
0.7-0.8	114
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
0.8421	Intermediate Similarity	NPD3882	Suspended
0.8412	Intermediate Similarity	NPD2801	Approved
0.8352	Intermediate Similarity	NPD7473	Discontinued
0.8333	Intermediate Similarity	NPD1247	Approved
0.8286	Intermediate Similarity	NPD6232	Discontinued
0.8276	Intermediate Similarity	NPD5494	Approved
0.8198	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD5844	Phase 1
0.814	Intermediate Similarity	NPD1934	Approved
0.8107	Intermediate Similarity	NPD1512	Approved
0.809	Intermediate Similarity	NPD6166	Phase 2
0.809	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3818	Discontinued
0.7988	Intermediate Similarity	NPD1511	Approved
0.7941	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD3926	Phase 2
0.7921	Intermediate Similarity	NPD6959	Discontinued
0.7886	Intermediate Similarity	NPD1465	Phase 2
0.7853	Intermediate Similarity	NPD3749	Approved
0.7841	Intermediate Similarity	NPD3817	Phase 2
0.7826	Intermediate Similarity	NPD6559	Discontinued
0.7816	Intermediate Similarity	NPD6599	Discontinued
0.7809	Intermediate Similarity	NPD919	Approved
0.7797	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD3226	Approved
0.7753	Intermediate Similarity	NPD7075	Discontinued
0.7751	Intermediate Similarity	NPD2800	Approved
0.774	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD2532	Approved
0.7733	Intermediate Similarity	NPD2533	Approved
0.7733	Intermediate Similarity	NPD2534	Approved
0.7725	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD8434	Phase 2
0.7684	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7819	Suspended
0.763	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7074	Phase 3
0.7619	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD4380	Phase 2
0.7611	Intermediate Similarity	NPD6234	Discontinued
0.7581	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD6797	Phase 2
0.7571	Intermediate Similarity	NPD7411	Suspended
0.7568	Intermediate Similarity	NPD7054	Approved
0.7566	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD7251	Discontinued
0.7528	Intermediate Similarity	NPD6801	Discontinued
0.7527	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6799	Approved
0.7471	Intermediate Similarity	NPD6099	Approved
0.7471	Intermediate Similarity	NPD6100	Approved
0.7471	Intermediate Similarity	NPD7390	Discontinued
0.7446	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5402	Approved
0.7442	Intermediate Similarity	NPD1243	Approved
0.743	Intermediate Similarity	NPD37	Approved
0.7427	Intermediate Similarity	NPD1471	Phase 3
0.7427	Intermediate Similarity	NPD2344	Approved
0.7419	Intermediate Similarity	NPD3751	Discontinued
0.7412	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4965	Approved
0.7403	Intermediate Similarity	NPD4966	Approved
0.7403	Intermediate Similarity	NPD4967	Phase 2
0.7396	Intermediate Similarity	NPD1607	Approved
0.7384	Intermediate Similarity	NPD1549	Phase 2
0.7384	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD943	Approved
0.738	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4111	Phase 1
0.7345	Intermediate Similarity	NPD920	Approved
0.7337	Intermediate Similarity	NPD7199	Phase 2
0.733	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD2346	Discontinued
0.7326	Intermediate Similarity	NPD7228	Approved
0.731	Intermediate Similarity	NPD1510	Phase 2
0.7308	Intermediate Similarity	NPD7768	Phase 2
0.7299	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3750	Approved
0.7297	Intermediate Similarity	NPD3787	Discontinued
0.7286	Intermediate Similarity	NPD6779	Approved
0.7286	Intermediate Similarity	NPD6780	Approved
0.7286	Intermediate Similarity	NPD6778	Approved
0.7286	Intermediate Similarity	NPD6777	Approved
0.7286	Intermediate Similarity	NPD6776	Approved
0.7286	Intermediate Similarity	NPD6781	Approved
0.7286	Intermediate Similarity	NPD6782	Approved
0.7278	Intermediate Similarity	NPD1240	Approved
0.7267	Intermediate Similarity	NPD2935	Discontinued
0.7267	Intermediate Similarity	NPD2796	Approved
0.7257	Intermediate Similarity	NPD2309	Approved
0.7254	Intermediate Similarity	NPD8150	Discontinued
0.7247	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5710	Approved
0.7204	Intermediate Similarity	NPD5711	Approved
0.72	Intermediate Similarity	NPD4628	Phase 3
0.719	Intermediate Similarity	NPD4665	Approved
0.7188	Intermediate Similarity	NPD8313	Approved
0.7188	Intermediate Similarity	NPD8312	Approved
0.7178	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD4583	Approved
0.7143	Intermediate Similarity	NPD4582	Approved
0.7135	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD2403	Approved
0.7123	Intermediate Similarity	NPD7907	Approved
0.7119	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7229	Phase 3
0.711	Intermediate Similarity	NPD2799	Discontinued
0.7104	Intermediate Similarity	NPD5760	Phase 2
0.7104	Intermediate Similarity	NPD5761	Phase 2
0.7094	Intermediate Similarity	NPD7698	Approved
0.7094	Intermediate Similarity	NPD4002	Approved
0.7094	Intermediate Similarity	NPD4004	Approved
0.7094	Intermediate Similarity	NPD7697	Approved
0.7094	Intermediate Similarity	NPD7696	Phase 3
0.7093	Intermediate Similarity	NPD6651	Approved
0.7087	Intermediate Similarity	NPD8151	Discontinued
0.7083	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7871	Phase 2
0.7059	Intermediate Similarity	NPD7870	Phase 2
0.7056	Intermediate Similarity	NPD5403	Approved
0.7047	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7701	Phase 2
0.7035	Intermediate Similarity	NPD447	Suspended
0.7035	Intermediate Similarity	NPD6534	Approved
0.7035	Intermediate Similarity	NPD6535	Approved
0.7035	Intermediate Similarity	NPD230	Phase 1
0.7019	Intermediate Similarity	NPD7801	Approved
0.7011	Intermediate Similarity	NPD3748	Approved
0.7006	Intermediate Similarity	NPD7003	Approved
0.7005	Intermediate Similarity	NPD4287	Approved
0.7	Intermediate Similarity	NPD4625	Phase 3
0.6995	Remote Similarity	NPD2493	Approved
0.6995	Remote Similarity	NPD2494	Approved
0.6983	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7458	Discontinued
0.6971	Remote Similarity	NPD7874	Approved
0.6971	Remote Similarity	NPD5408	Approved
0.6971	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD1551	Phase 2
0.6971	Remote Similarity	NPD5406	Approved
0.6971	Remote Similarity	NPD5404	Approved
0.6971	Remote Similarity	NPD5405	Approved
0.6966	Remote Similarity	NPD6190	Approved
0.6963	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4580	Approved
0.6944	Remote Similarity	NPD5401	Approved
0.6938	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD7783	Phase 2
0.6931	Remote Similarity	NPD7700	Phase 2
0.6931	Remote Similarity	NPD7699	Phase 2
0.6912	Remote Similarity	NPD3450	Approved
0.6912	Remote Similarity	NPD3452	Approved
0.6907	Remote Similarity	NPD7240	Approved
0.6888	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2488	Approved
0.6884	Remote Similarity	NPD2490	Approved
0.6879	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1613	Approved
0.6878	Remote Similarity	NPD8127	Discontinued
0.6878	Remote Similarity	NPD2491	Approved
0.6878	Remote Similarity	NPD3057	Approved
0.6878	Remote Similarity	NPD6823	Phase 2
0.6875	Remote Similarity	NPD2163	Approved
0.6864	Remote Similarity	NPD1470	Approved
0.6861	Remote Similarity	NPD7048	Phase 3
0.686	Remote Similarity	NPD2313	Discontinued
0.6856	Remote Similarity	NPD5953	Discontinued
0.6839	Remote Similarity	NPD7286	Phase 2
0.6836	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7685	Pre-registration
0.6821	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.682	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6273	Approved
0.6808	Remote Similarity	NPD7047	Phase 3
0.6805	Remote Similarity	NPD6696	Suspended
0.6802	Remote Similarity	NPD3027	Phase 3
0.6798	Remote Similarity	NPD2975	Approved
0.6798	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD2974	Approved
0.6798	Remote Similarity	NPD2973	Approved
0.6796	Remote Similarity	NPD3533	Approved
0.6796	Remote Similarity	NPD3448	Approved
0.6796	Remote Similarity	NPD2972	Approved
0.6791	Remote Similarity	NPD2296	Approved
0.6782	Remote Similarity	NPD4060	Phase 1
0.6763	Remote Similarity	NPD3764	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