NPASS Compound

Structure

CID224345 OpenBabel06191716022D 24 26 0 0 1 0 0 0 0 0999 V2000 2.8473 2.1423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4319 0.3767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9833 0.3525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9171 1.8931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6679 -1.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5019 -1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 -1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6679 0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9630 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8340 1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6679 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4648 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 0.9630 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5019 -0.4815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8340 -0.4815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8340 2.4074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9463 0.3525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9463 -1.3154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 4 19 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 17 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 14 1 0 0 0 0 13 20 1 6 0 0 0 14 21 2 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 2 1 1 0 0 0 18 3 1 6 0 0 0 19 20 1 6 0 0 0 20 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	356.058
LogP:	2.199
LogD:	1.262
LogS:	-3.788
# Rotatable Bonds:	2
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.757
Synthetic Accessibility Score:	4.789
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.202
MDCK Permeability:	2.406068961136043e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.101
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.797
Plasma Protein Binding (PPB):	91.00475311279297%
Volume Distribution (VD):	0.318
Pgp-substrate:	9.313335418701172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.572
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.777
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.402
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.165
CYP3A4-inhibitor:	0.181
CYP3A4-substrate:	0.12

ADMET: Excretion

Clearance (CL):	1.141
Half-life (T1/2):	0.632

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.198
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.157
Carcinogencity:	0.061
Eye Corrosion:	0.03
Eye Irritation:	0.427
Respiratory Toxicity:	0.053

Download Data

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

Natural Product: NPC224345

Natural Product ID:	NPC224345
*Common Name:**	Acanthokoreoic Acid A
IUPAC Name:	(1R,4aR,4bR,7R,8aR)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-9-oxo-3,4,5,6,8,8a,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	QWUJSFMPRYDMES-LBDOQNLRSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-5-17(2)9-10-20(24)13(12-17)14(21)11-15-18(3,16(22)23)7-6-8-19(15,20)4/h5,13,15,24H,1,6-12H2,2-4H3,(H,22,23)/t13-,15?,17+,18+,19+,20+/m0/s1
SMILES:	C=C[C@]1(C)CC[C@]2([C@@H](C1)C(=O)CC1[C@@](C)(CCC[C@@]21C)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL207043
PubChem CID:	10914619
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO25047	Eleutherococcus koreanus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	30000.0	nM	PMID[507675]

☑ 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 NPC224345 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	220
0.1-0.2	1889
0.2-0.3	6882
0.3-0.4	14220
0.4-0.5	8951
0.5-0.6	5674
0.6-0.7	3960
0.7-0.8	883
0.8-0.85	15
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8625	High Similarity	NPC104806
0.8481	Intermediate Similarity	NPC177826
0.8375	Intermediate Similarity	NPC38426
0.8375	Intermediate Similarity	NPC162164
0.8261	Intermediate Similarity	NPC470387
0.8222	Intermediate Similarity	NPC198242
0.8222	Intermediate Similarity	NPC211403
0.8132	Intermediate Similarity	NPC131840
0.8085	Intermediate Similarity	NPC474724
0.8043	Intermediate Similarity	NPC470385
0.8043	Intermediate Similarity	NPC470386
0.8043	Intermediate Similarity	NPC475118
0.7957	Intermediate Similarity	NPC470232
0.7957	Intermediate Similarity	NPC266431
0.7957	Intermediate Similarity	NPC470229
0.7917	Intermediate Similarity	NPC71706
0.7912	Intermediate Similarity	NPC263977
0.7907	Intermediate Similarity	NPC20096
0.7907	Intermediate Similarity	NPC48673
0.7895	Intermediate Similarity	NPC477653
0.7872	Intermediate Similarity	NPC223169
0.7872	Intermediate Similarity	NPC329910
0.7857	Intermediate Similarity	NPC112463
0.7857	Intermediate Similarity	NPC472746
0.7849	Intermediate Similarity	NPC474529
0.7826	Intermediate Similarity	NPC327515
0.7816	Intermediate Similarity	NPC476935
0.7778	Intermediate Similarity	NPC298904
0.7778	Intermediate Similarity	NPC476932
0.7778	Intermediate Similarity	NPC259009
0.7766	Intermediate Similarity	NPC197158
0.7766	Intermediate Similarity	NPC288906
0.7766	Intermediate Similarity	NPC217329
0.7766	Intermediate Similarity	NPC471624
0.7766	Intermediate Similarity	NPC263135
0.7755	Intermediate Similarity	NPC216114
0.775	Intermediate Similarity	NPC470956
0.7742	Intermediate Similarity	NPC224060
0.7742	Intermediate Similarity	NPC244356
0.7727	Intermediate Similarity	NPC107253
0.7717	Intermediate Similarity	NPC80401
0.7711	Intermediate Similarity	NPC255168
0.7708	Intermediate Similarity	NPC471038
0.7701	Intermediate Similarity	NPC221647
0.7692	Intermediate Similarity	NPC124927
0.7692	Intermediate Similarity	NPC475101
0.7692	Intermediate Similarity	NPC476427
0.7684	Intermediate Similarity	NPC140242
0.7684	Intermediate Similarity	NPC234564
0.7684	Intermediate Similarity	NPC477853
0.7677	Intermediate Similarity	NPC98603
0.7677	Intermediate Similarity	NPC201763
0.7677	Intermediate Similarity	NPC84928
0.7667	Intermediate Similarity	NPC470415
0.766	Intermediate Similarity	NPC469982
0.766	Intermediate Similarity	NPC47853
0.764	Intermediate Similarity	NPC219535
0.764	Intermediate Similarity	NPC237938
0.7634	Intermediate Similarity	NPC250753
0.7634	Intermediate Similarity	NPC476934
0.7634	Intermediate Similarity	NPC470230
0.7634	Intermediate Similarity	NPC476168
0.7629	Intermediate Similarity	NPC470388
0.7629	Intermediate Similarity	NPC477655
0.7629	Intermediate Similarity	NPC477656
0.7619	Intermediate Similarity	NPC201027
0.7614	Intermediate Similarity	NPC302661
0.7614	Intermediate Similarity	NPC238991
0.7609	Intermediate Similarity	NPC475108
0.7604	Intermediate Similarity	NPC473456
0.7595	Intermediate Similarity	NPC469791
0.7586	Intermediate Similarity	NPC26139
0.7586	Intermediate Similarity	NPC469637
0.7586	Intermediate Similarity	NPC37038
0.7582	Intermediate Similarity	NPC153604
0.7579	Intermediate Similarity	NPC98639
0.7579	Intermediate Similarity	NPC473240
0.7576	Intermediate Similarity	NPC312900
0.7558	Intermediate Similarity	NPC476810
0.7556	Intermediate Similarity	NPC471034
0.7556	Intermediate Similarity	NPC190704
0.7553	Intermediate Similarity	NPC199543
0.7553	Intermediate Similarity	NPC144739
0.7553	Intermediate Similarity	NPC181594
0.7551	Intermediate Similarity	NPC46848
0.7551	Intermediate Similarity	NPC289148
0.7551	Intermediate Similarity	NPC163963
0.7551	Intermediate Similarity	NPC295276
0.7551	Intermediate Similarity	NPC52899
0.7529	Intermediate Similarity	NPC78935
0.7526	Intermediate Similarity	NPC474793
0.7526	Intermediate Similarity	NPC472028
0.7526	Intermediate Similarity	NPC114274
0.7526	Intermediate Similarity	NPC477854
0.7525	Intermediate Similarity	NPC263729
0.75	Intermediate Similarity	NPC29410
0.75	Intermediate Similarity	NPC48107
0.75	Intermediate Similarity	NPC200054
0.75	Intermediate Similarity	NPC475036
0.75	Intermediate Similarity	NPC46610
0.75	Intermediate Similarity	NPC18819
0.75	Intermediate Similarity	NPC219353
0.75	Intermediate Similarity	NPC269492
0.75	Intermediate Similarity	NPC50847
0.75	Intermediate Similarity	NPC474558
0.75	Intermediate Similarity	NPC476327
0.75	Intermediate Similarity	NPC13949
0.75	Intermediate Similarity	NPC476071
0.75	Intermediate Similarity	NPC473217
0.75	Intermediate Similarity	NPC476318
0.7475	Intermediate Similarity	NPC214946
0.7475	Intermediate Similarity	NPC271980
0.7475	Intermediate Similarity	NPC286519
0.7475	Intermediate Similarity	NPC304832
0.7475	Intermediate Similarity	NPC88203
0.7475	Intermediate Similarity	NPC148628
0.7475	Intermediate Similarity	NPC275990
0.7475	Intermediate Similarity	NPC76866
0.7475	Intermediate Similarity	NPC193934
0.7475	Intermediate Similarity	NPC246736
0.7474	Intermediate Similarity	NPC148964
0.7474	Intermediate Similarity	NPC292374
0.7474	Intermediate Similarity	NPC289539
0.7474	Intermediate Similarity	NPC261333
0.7474	Intermediate Similarity	NPC64006
0.7474	Intermediate Similarity	NPC111524
0.7474	Intermediate Similarity	NPC91772
0.7474	Intermediate Similarity	NPC104371
0.7474	Intermediate Similarity	NPC129004
0.7474	Intermediate Similarity	NPC191094
0.7474	Intermediate Similarity	NPC101233
0.7474	Intermediate Similarity	NPC153775
0.7474	Intermediate Similarity	NPC302008
0.7474	Intermediate Similarity	NPC215271
0.7474	Intermediate Similarity	NPC29247
0.7473	Intermediate Similarity	NPC248216
0.7473	Intermediate Similarity	NPC83242
0.7473	Intermediate Similarity	NPC73038
0.7473	Intermediate Similarity	NPC120395
0.7471	Intermediate Similarity	NPC231431
0.747	Intermediate Similarity	NPC472309
0.7451	Intermediate Similarity	NPC208461
0.7451	Intermediate Similarity	NPC289702
0.7451	Intermediate Similarity	NPC163216
0.7449	Intermediate Similarity	NPC37047
0.7449	Intermediate Similarity	NPC41971
0.7449	Intermediate Similarity	NPC55503
0.7449	Intermediate Similarity	NPC287676
0.7449	Intermediate Similarity	NPC156324
0.7449	Intermediate Similarity	NPC180733
0.7449	Intermediate Similarity	NPC117685
0.7449	Intermediate Similarity	NPC94906
0.7447	Intermediate Similarity	NPC6255
0.7447	Intermediate Similarity	NPC198054
0.7447	Intermediate Similarity	NPC324341
0.7447	Intermediate Similarity	NPC155120
0.7447	Intermediate Similarity	NPC966
0.7447	Intermediate Similarity	NPC228784
0.7447	Intermediate Similarity	NPC288833
0.7447	Intermediate Similarity	NPC475708
0.7447	Intermediate Similarity	NPC282616
0.7447	Intermediate Similarity	NPC471588
0.7447	Intermediate Similarity	NPC299185
0.7444	Intermediate Similarity	NPC477434
0.7442	Intermediate Similarity	NPC474433
0.7442	Intermediate Similarity	NPC471035
0.7442	Intermediate Similarity	NPC66105
0.7442	Intermediate Similarity	NPC212661
0.7423	Intermediate Similarity	NPC10864
0.7423	Intermediate Similarity	NPC189880
0.7423	Intermediate Similarity	NPC253586
0.7423	Intermediate Similarity	NPC170978
0.7419	Intermediate Similarity	NPC57954
0.7419	Intermediate Similarity	NPC213832
0.7419	Intermediate Similarity	NPC69627
0.7419	Intermediate Similarity	NPC471043
0.7419	Intermediate Similarity	NPC59682
0.7416	Intermediate Similarity	NPC474605
0.7416	Intermediate Similarity	NPC476292
0.7416	Intermediate Similarity	NPC469325
0.7412	Intermediate Similarity	NPC279666
0.7412	Intermediate Similarity	NPC39362
0.7412	Intermediate Similarity	NPC192540
0.74	Intermediate Similarity	NPC139347
0.74	Intermediate Similarity	NPC209298
0.74	Intermediate Similarity	NPC230918
0.74	Intermediate Similarity	NPC122811
0.74	Intermediate Similarity	NPC275583
0.74	Intermediate Similarity	NPC87927
0.74	Intermediate Similarity	NPC90177
0.74	Intermediate Similarity	NPC469985
0.74	Intermediate Similarity	NPC277074
0.7396	Intermediate Similarity	NPC84018
0.7396	Intermediate Similarity	NPC139570
0.7396	Intermediate Similarity	NPC231060
0.7396	Intermediate Similarity	NPC41070
0.7396	Intermediate Similarity	NPC279974
0.7396	Intermediate Similarity	NPC148523
0.7396	Intermediate Similarity	NPC138245
0.7396	Intermediate Similarity	NPC266899

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 NPC224345 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	2426
0.2-0.3	3955
0.3-0.4	1677
0.4-0.5	484
0.5-0.6	194
0.6-0.7	176
0.7-0.8	15
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
0.7451	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3573	Approved
0.7283	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7515	Phase 2
0.7262	Intermediate Similarity	NPD6081	Approved
0.7209	Intermediate Similarity	NPD3703	Phase 2
0.7174	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6118	Approved
0.7159	Intermediate Similarity	NPD6115	Approved
0.7159	Intermediate Similarity	NPD6114	Approved
0.7159	Intermediate Similarity	NPD6697	Approved
0.7113	Intermediate Similarity	NPD7748	Approved
0.7073	Intermediate Similarity	NPD4224	Phase 2
0.697	Remote Similarity	NPD7614	Phase 1
0.6932	Remote Similarity	NPD6117	Approved
0.6907	Remote Similarity	NPD6079	Approved
0.6907	Remote Similarity	NPD8035	Phase 2
0.6907	Remote Similarity	NPD8034	Phase 2
0.6905	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5360	Phase 3
0.69	Remote Similarity	NPD7902	Approved
0.6875	Remote Similarity	NPD5328	Approved
0.6875	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5697	Approved
0.6854	Remote Similarity	NPD6116	Phase 1
0.6822	Remote Similarity	NPD4634	Approved
0.68	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5222	Approved
0.68	Remote Similarity	NPD5221	Approved
0.6792	Remote Similarity	NPD6011	Approved
0.6792	Remote Similarity	NPD6899	Approved
0.6792	Remote Similarity	NPD6881	Approved
0.6789	Remote Similarity	NPD4632	Approved
0.6765	Remote Similarity	NPD5285	Approved
0.6765	Remote Similarity	NPD5286	Approved
0.6765	Remote Similarity	NPD4696	Approved
0.6762	Remote Similarity	NPD5739	Approved
0.6762	Remote Similarity	NPD6675	Approved
0.6762	Remote Similarity	NPD6402	Approved
0.6762	Remote Similarity	NPD7128	Approved
0.6737	Remote Similarity	NPD3618	Phase 1
0.6735	Remote Similarity	NPD5284	Approved
0.6735	Remote Similarity	NPD5281	Approved
0.6735	Remote Similarity	NPD6411	Approved
0.6733	Remote Similarity	NPD5173	Approved
0.6733	Remote Similarity	NPD4755	Approved
0.6729	Remote Similarity	NPD6014	Approved
0.6729	Remote Similarity	NPD6012	Approved
0.6729	Remote Similarity	NPD6013	Approved
0.6726	Remote Similarity	NPD6319	Approved
0.6705	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5223	Approved
0.6698	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD4758	Discontinued
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD6921	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6636	Remote Similarity	NPD7320	Approved
0.6635	Remote Similarity	NPD5224	Approved
0.6635	Remote Similarity	NPD5226	Approved
0.6635	Remote Similarity	NPD5211	Phase 2
0.6635	Remote Similarity	NPD5225	Approved
0.6635	Remote Similarity	NPD4633	Approved
0.6634	Remote Similarity	NPD4697	Phase 3
0.663	Remote Similarity	NPD4695	Discontinued
0.6628	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6009	Approved
0.6606	Remote Similarity	NPD6847	Approved
0.6606	Remote Similarity	NPD8130	Phase 1
0.6606	Remote Similarity	NPD6650	Approved
0.6606	Remote Similarity	NPD6617	Approved
0.6606	Remote Similarity	NPD6869	Approved
0.6606	Remote Similarity	NPD6649	Approved
0.6604	Remote Similarity	NPD6008	Approved
0.6602	Remote Similarity	NPD7640	Approved
0.6602	Remote Similarity	NPD4700	Approved
0.6602	Remote Similarity	NPD7639	Approved
0.66	Remote Similarity	NPD7900	Approved
0.66	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4788	Approved
0.6574	Remote Similarity	NPD6372	Approved
0.6574	Remote Similarity	NPD6373	Approved
0.6571	Remote Similarity	NPD5175	Approved
0.6571	Remote Similarity	NPD5174	Approved
0.6562	Remote Similarity	NPD4519	Discontinued
0.6562	Remote Similarity	NPD4623	Approved
0.6545	Remote Similarity	NPD8297	Approved
0.6545	Remote Similarity	NPD6882	Approved
0.6535	Remote Similarity	NPD4629	Approved
0.6535	Remote Similarity	NPD5210	Approved
0.6531	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6101	Approved
0.6526	Remote Similarity	NPD4197	Approved
0.6526	Remote Similarity	NPD4786	Approved
0.6509	Remote Similarity	NPD5141	Approved
0.65	Remote Similarity	NPD5778	Approved
0.65	Remote Similarity	NPD4202	Approved
0.65	Remote Similarity	NPD5779	Approved
0.6496	Remote Similarity	NPD7492	Approved
0.6477	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7736	Approved
0.6471	Remote Similarity	NPD7732	Phase 3
0.6458	Remote Similarity	NPD5329	Approved
0.6455	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3702	Approved
0.6441	Remote Similarity	NPD6616	Approved
0.6435	Remote Similarity	NPD6054	Approved
0.6415	Remote Similarity	NPD4754	Approved
0.6413	Remote Similarity	NPD3617	Approved
0.6413	Remote Similarity	NPD5364	Discontinued
0.641	Remote Similarity	NPD8328	Phase 3
0.6408	Remote Similarity	NPD6084	Phase 2
0.6408	Remote Similarity	NPD6083	Phase 2
0.6392	Remote Similarity	NPD6098	Approved
0.6392	Remote Similarity	NPD4688	Approved
0.6392	Remote Similarity	NPD4690	Approved
0.6392	Remote Similarity	NPD4693	Phase 3
0.6392	Remote Similarity	NPD5690	Phase 2
0.6392	Remote Similarity	NPD4689	Approved
0.6392	Remote Similarity	NPD5205	Approved
0.6392	Remote Similarity	NPD4138	Approved
0.6387	Remote Similarity	NPD7078	Approved
0.6379	Remote Similarity	NPD6016	Approved
0.6379	Remote Similarity	NPD5983	Phase 2
0.6379	Remote Similarity	NPD6015	Approved
0.6373	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5695	Phase 3
0.6364	Remote Similarity	NPD6080	Approved
0.6364	Remote Similarity	NPD4753	Phase 2
0.6364	Remote Similarity	NPD6673	Approved
0.6364	Remote Similarity	NPD6904	Approved
0.6354	Remote Similarity	NPD3665	Phase 1
0.6354	Remote Similarity	NPD3133	Approved
0.6354	Remote Similarity	NPD3666	Approved
0.6354	Remote Similarity	NPD3668	Phase 3
0.633	Remote Similarity	NPD4730	Approved
0.633	Remote Similarity	NPD4729	Approved
0.6325	Remote Similarity	NPD5988	Approved
0.6325	Remote Similarity	NPD6370	Approved
0.6316	Remote Similarity	NPD6317	Approved
0.6316	Remote Similarity	NPD7115	Discovery
0.6316	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4768	Approved
0.6296	Remote Similarity	NPD4767	Approved
0.6293	Remote Similarity	NPD6059	Approved
0.6277	Remote Similarity	NPD7525	Registered
0.6275	Remote Similarity	NPD6001	Approved
0.6271	Remote Similarity	NPD7604	Phase 2
0.6263	Remote Similarity	NPD6672	Approved
0.6263	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5208	Approved
0.6263	Remote Similarity	NPD5737	Approved
0.6261	Remote Similarity	NPD6314	Approved
0.6261	Remote Similarity	NPD6313	Approved
0.6261	Remote Similarity	NPD6335	Approved
0.625	Remote Similarity	NPD3698	Phase 2
0.625	Remote Similarity	NPD8293	Discontinued
0.6238	Remote Similarity	NPD5693	Phase 1
0.6238	Remote Similarity	NPD5694	Approved
0.6228	Remote Similarity	NPD6868	Approved
0.6228	Remote Similarity	NPD6274	Approved
0.6224	Remote Similarity	NPD4694	Approved
0.6224	Remote Similarity	NPD7521	Approved
0.6224	Remote Similarity	NPD7334	Approved
0.6224	Remote Similarity	NPD5280	Approved
0.6224	Remote Similarity	NPD6684	Approved
0.6224	Remote Similarity	NPD6409	Approved
0.6224	Remote Similarity	NPD7146	Approved
0.6224	Remote Similarity	NPD5330	Approved
0.6216	Remote Similarity	NPD5248	Approved
0.6216	Remote Similarity	NPD5135	Approved
0.6216	Remote Similarity	NPD5250	Approved
0.6216	Remote Similarity	NPD5247	Approved
0.6216	Remote Similarity	NPD5249	Phase 3
0.6216	Remote Similarity	NPD5251	Approved
0.6216	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5169	Approved
0.6211	Remote Similarity	NPD4139	Approved
0.6211	Remote Similarity	NPD4692	Approved
0.6207	Remote Similarity	NPD7101	Approved
0.6207	Remote Similarity	NPD7100	Approved
0.6182	Remote Similarity	NPD5168	Approved
0.6182	Remote Similarity	NPD5128	Approved
0.618	Remote Similarity	NPD4789	Approved
0.618	Remote Similarity	NPD4244	Approved
0.618	Remote Similarity	NPD4245	Approved
0.617	Remote Similarity	NPD4195	Approved
0.6168	Remote Similarity	NPD5091	Approved
0.6168	Remote Similarity	NPD7632	Discontinued
0.6167	Remote Similarity	NPD6336	Discontinued
0.6163	Remote Similarity	NPD3171	Clinical (unspecified phase)

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