NPASS Compound

Structure

NPC473975 OpenBabel07101718292D 36 40 0 0 1 0 0 0 0 0999 V2000 -3.2741 -2.8557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7107 -5.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3462 -5.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1372 1.7825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0036 -1.8292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6564 -0.6030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7754 1.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7728 -3.3435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -3.6449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3462 -1.5786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3462 -2.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3462 -2.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2596 -5.0240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3462 -4.5054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8330 1.6805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0830 -3.3435 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5013 -3.0420 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3462 -1.5786 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7728 -0.7893 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6564 -1.5786 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0830 -0.7893 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7728 0.7893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6564 -2.5542 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5013 -1.0908 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8449 0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8449 -0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8330 -5.8133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1911 -4.0176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4065 2.4698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0742 1.7171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6564 -4.1327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5013 -4.0176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2299 0.7893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3462 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3462 -0.6030 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 12 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 7 25 1 0 0 0 0 8 9 1 0 0 0 0 8 12 1 0 0 0 0 9 16 1 0 0 0 0 10 12 2 0 0 0 0 10 19 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 13 27 2 0 0 0 0 13 31 1 0 0 0 0 14 28 2 0 0 0 0 14 32 1 0 0 0 0 15 29 2 0 0 0 0 15 33 1 0 0 0 0 16 23 1 6 0 0 0 16 31 1 0 0 0 0 17 23 1 6 0 0 0 17 32 1 0 0 0 0 18 24 1 1 0 0 0 18 35 1 0 0 0 0 19 26 1 6 0 0 0 19 34 1 0 0 0 0 20 21 1 0 0 0 0 20 23 1 1 0 0 0 20 24 1 0 0 0 0 21 26 1 6 0 0 0 21 33 1 0 0 0 0 22 25 1 0 0 0 0 22 30 2 0 0 0 0 22 34 1 0 0 0 0 23 5 1 1 0 0 0 24 6 1 6 0 0 0 24 35 1 0 0 0 0 25 26 1 6 0 0 0 25 36 1 0 0 0 0 26 36 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.22
Volume:	490.19
LogP:	2.467
LogD:	1.735
LogS:	-4.715
# Rotatable Bonds:	6
TPSA:	130.26
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.243
Synthetic Accessibility Score:	6.079
Fsp3:	0.769
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.172
MDCK Permeability:	0.00014046842989046127
Pgp-inhibitor:	0.999
Pgp-substrate:	0.101
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.175
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.85
Plasma Protein Binding (PPB):	47.338836669921875%
Volume Distribution (VD):	1.537
Pgp-substrate:	52.88188552856445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.158
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.571
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	3.386
Half-life (T1/2):	0.518

ADMET: Toxicity

hERG Blockers:	0.171
Human Hepatotoxicity (H-HT):	0.953
Drug-inuced Liver Injury (DILI):	0.903
AMES Toxicity:	0.827
Rat Oral Acute Toxicity:	0.841
Maximum Recommended Daily Dose:	0.693
Skin Sensitization:	0.666
Carcinogencity:	0.502
Eye Corrosion:	0.068
Eye Irritation:	0.044
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC473975

Natural Product ID:	NPC473975
*Common Name:**	ANJHIXLYXNTIDW-LJFFYTAJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ANJHIXLYXNTIDW-LJFFYTAJSA-N
Standard InCHI:	InChI=1S/C26H34O10/c1-12-8-9-16(31-13(2)27)23(5)17(32-14(3)28)11-18-24(6,35-18)20(23)21(33-15(4)29)26-19(10-12)34-22(30)25(26,7)36-26/h10,16-21H,8-9,11H2,1-7H3/b12-10-/t16-,17+,18+,19+,20-,21-,23+,24+,25-,26+/m1/s1
SMILES:	CC(=O)O[C@@H]1CC/C(=C[C@H]2[C@@]3([C@@H]([C@@H]4[C@]1(C)[C@@H](OC(=O)C)C[C@H]1[C@]4(C)O1)OC(=O)C)O[C@]3(C)C(=O)O2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456944
PubChem CID:	44584200
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640510]
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	Formosan gorgonian	n.a.	PMID[8984161]
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	Indonesian Gorgonian	n.a.	PMID[9548870]

☑ 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
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.59	ug ml-1	PMID[524220]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	24.45	ug ml-1	PMID[524220]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	17.39	ug ml-1	PMID[524220]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	10.07	ug ml-1	PMID[524220]

☑ 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 NPC473975 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	276
0.1-0.2	1714
0.2-0.3	5277
0.3-0.4	9788
0.4-0.5	13235
0.5-0.6	7864
0.6-0.7	3781
0.7-0.8	679
0.8-0.85	57
0.85-0.9	8
0.9-0.95	9
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473594
1.0	High Similarity	NPC474586
1.0	High Similarity	NPC473843
0.9902	High Similarity	NPC194619
0.9703	High Similarity	NPC475587
0.9703	High Similarity	NPC475510
0.9608	High Similarity	NPC473939
0.9608	High Similarity	NPC473595
0.9528	High Similarity	NPC474333
0.9439	High Similarity	NPC296822
0.9423	High Similarity	NPC281624
0.9245	High Similarity	NPC473877
0.9216	High Similarity	NPC19239
0.9216	High Similarity	NPC474166
0.9048	High Similarity	NPC94377
0.8962	High Similarity	NPC42662
0.8785	High Similarity	NPC475922
0.8727	High Similarity	NPC73314
0.8704	High Similarity	NPC115257
0.8704	High Similarity	NPC161816
0.8649	High Similarity	NPC476711
0.8649	High Similarity	NPC476710
0.8571	High Similarity	NPC476713
0.8571	High Similarity	NPC476712
0.8544	High Similarity	NPC471140
0.8505	High Similarity	NPC16313
0.8505	High Similarity	NPC475802
0.8505	High Similarity	NPC9303
0.8482	Intermediate Similarity	NPC477509
0.8426	Intermediate Similarity	NPC326994
0.8426	Intermediate Similarity	NPC72813
0.8426	Intermediate Similarity	NPC474421
0.8426	Intermediate Similarity	NPC324327
0.8426	Intermediate Similarity	NPC194620
0.8421	Intermediate Similarity	NPC470186
0.8396	Intermediate Similarity	NPC183571
0.8349	Intermediate Similarity	NPC169888
0.8349	Intermediate Similarity	NPC474664
0.8349	Intermediate Similarity	NPC14862
0.8349	Intermediate Similarity	NPC233379
0.8349	Intermediate Similarity	NPC55972
0.8349	Intermediate Similarity	NPC327286
0.8318	Intermediate Similarity	NPC474165
0.8318	Intermediate Similarity	NPC69171
0.8304	Intermediate Similarity	NPC477126
0.8302	Intermediate Similarity	NPC477511
0.8302	Intermediate Similarity	NPC264477
0.8273	Intermediate Similarity	NPC15218
0.8257	Intermediate Similarity	NPC469558
0.8257	Intermediate Similarity	NPC474716
0.8241	Intermediate Similarity	NPC477127
0.8205	Intermediate Similarity	NPC282003
0.8205	Intermediate Similarity	NPC188222
0.8205	Intermediate Similarity	NPC310035
0.8158	Intermediate Similarity	NPC270478
0.8148	Intermediate Similarity	NPC4620
0.8142	Intermediate Similarity	NPC33360
0.8136	Intermediate Similarity	NPC303006
0.8131	Intermediate Similarity	NPC98225
0.8131	Intermediate Similarity	NPC476478
0.8077	Intermediate Similarity	NPC161998
0.8073	Intermediate Similarity	NPC471143
0.8073	Intermediate Similarity	NPC220964
0.8073	Intermediate Similarity	NPC477510
0.8073	Intermediate Similarity	NPC475676
0.8056	Intermediate Similarity	NPC471148
0.8053	Intermediate Similarity	NPC317687
0.8053	Intermediate Similarity	NPC471933
0.8037	Intermediate Similarity	NPC477512
0.8034	Intermediate Similarity	NPC475003
0.8	Intermediate Similarity	NPC103088
0.8	Intermediate Similarity	NPC470975
0.8	Intermediate Similarity	NPC470979
0.7967	Intermediate Similarity	NPC470185
0.7965	Intermediate Similarity	NPC317107
0.7946	Intermediate Similarity	NPC469370
0.7946	Intermediate Similarity	NPC471934
0.7944	Intermediate Similarity	NPC264378
0.7931	Intermediate Similarity	NPC473590
0.7931	Intermediate Similarity	NPC58662
0.7928	Intermediate Similarity	NPC180744
0.7928	Intermediate Similarity	NPC477513
0.7925	Intermediate Similarity	NPC17585
0.7905	Intermediate Similarity	NPC471147
0.789	Intermediate Similarity	NPC474709
0.7876	Intermediate Similarity	NPC253906
0.787	Intermediate Similarity	NPC469551
0.7864	Intermediate Similarity	NPC475971
0.7863	Intermediate Similarity	NPC240509
0.7857	Intermediate Similarity	NPC322903
0.7845	Intermediate Similarity	NPC470793
0.7833	Intermediate Similarity	NPC472399
0.7833	Intermediate Similarity	NPC67251
0.7826	Intermediate Similarity	NPC89018
0.7807	Intermediate Similarity	NPC470467
0.7798	Intermediate Similarity	NPC164598
0.7798	Intermediate Similarity	NPC474339
0.7788	Intermediate Similarity	NPC475191
0.7778	Intermediate Similarity	NPC176513
0.7778	Intermediate Similarity	NPC469684
0.7778	Intermediate Similarity	NPC470775
0.7778	Intermediate Similarity	NPC208233
0.7759	Intermediate Similarity	NPC88867
0.7759	Intermediate Similarity	NPC226608
0.7739	Intermediate Similarity	NPC470468
0.7731	Intermediate Similarity	NPC4548
0.7731	Intermediate Similarity	NPC471126
0.7731	Intermediate Similarity	NPC157252
0.7731	Intermediate Similarity	NPC471128
0.7731	Intermediate Similarity	NPC145182
0.7724	Intermediate Similarity	NPC236999
0.7719	Intermediate Similarity	NPC475563
0.7719	Intermediate Similarity	NPC472215
0.7719	Intermediate Similarity	NPC475134
0.7719	Intermediate Similarity	NPC472214
0.7712	Intermediate Similarity	NPC470776
0.7706	Intermediate Similarity	NPC474718
0.7705	Intermediate Similarity	NPC225049
0.7699	Intermediate Similarity	NPC476479
0.7692	Intermediate Similarity	NPC474734
0.7692	Intermediate Similarity	NPC470466
0.7686	Intermediate Similarity	NPC105926
0.7686	Intermediate Similarity	NPC473802
0.7686	Intermediate Similarity	NPC91693
0.7686	Intermediate Similarity	NPC18945
0.7686	Intermediate Similarity	NPC265557
0.7685	Intermediate Similarity	NPC100912
0.7685	Intermediate Similarity	NPC474921
0.7679	Intermediate Similarity	NPC123726
0.7679	Intermediate Similarity	NPC284365
0.7672	Intermediate Similarity	NPC159333
0.7672	Intermediate Similarity	NPC470120
0.767	Intermediate Similarity	NPC266957
0.7667	Intermediate Similarity	NPC470779
0.7667	Intermediate Similarity	NPC52839
0.7667	Intermediate Similarity	NPC472401
0.7664	Intermediate Similarity	NPC476519
0.7661	Intermediate Similarity	NPC476851
0.7652	Intermediate Similarity	NPC475495
0.7652	Intermediate Similarity	NPC475480
0.7652	Intermediate Similarity	NPC475668
0.7652	Intermediate Similarity	NPC469656
0.7652	Intermediate Similarity	NPC469655
0.7652	Intermediate Similarity	NPC473921
0.7652	Intermediate Similarity	NPC474846
0.7647	Intermediate Similarity	NPC475520
0.7647	Intermediate Similarity	NPC472667
0.7642	Intermediate Similarity	NPC476598
0.7642	Intermediate Similarity	NPC470780
0.7642	Intermediate Similarity	NPC476597
0.7627	Intermediate Similarity	NPC53396
0.7627	Intermediate Similarity	NPC98249
0.7623	Intermediate Similarity	NPC473709
0.7623	Intermediate Similarity	NPC473919
0.7623	Intermediate Similarity	NPC24651
0.7623	Intermediate Similarity	NPC476729
0.7619	Intermediate Similarity	NPC475748
0.7615	Intermediate Similarity	NPC72647
0.7615	Intermediate Similarity	NPC107806
0.7611	Intermediate Similarity	NPC187435
0.7611	Intermediate Similarity	NPC67321
0.7603	Intermediate Similarity	NPC19464
0.7603	Intermediate Similarity	NPC312833
0.7603	Intermediate Similarity	NPC162009
0.7603	Intermediate Similarity	NPC257017
0.76	Intermediate Similarity	NPC476852
0.7593	Intermediate Similarity	NPC35498
0.7593	Intermediate Similarity	NPC209297
0.7593	Intermediate Similarity	NPC475380
0.7589	Intermediate Similarity	NPC258532
0.7589	Intermediate Similarity	NPC146731
0.7589	Intermediate Similarity	NPC283850
0.7586	Intermediate Similarity	NPC475391
0.7586	Intermediate Similarity	NPC473522
0.7586	Intermediate Similarity	NPC477093
0.7586	Intermediate Similarity	NPC269530
0.7586	Intermediate Similarity	NPC475277
0.7586	Intermediate Similarity	NPC42658
0.7586	Intermediate Similarity	NPC222834
0.7583	Intermediate Similarity	NPC143755
0.7581	Intermediate Similarity	NPC476859
0.7573	Intermediate Similarity	NPC50637
0.757	Intermediate Similarity	NPC140277
0.757	Intermediate Similarity	NPC476596
0.7568	Intermediate Similarity	NPC105725
0.7568	Intermediate Similarity	NPC476081
0.7565	Intermediate Similarity	NPC140409
0.7565	Intermediate Similarity	NPC156248
0.7565	Intermediate Similarity	NPC11491
0.7563	Intermediate Similarity	NPC472397
0.7563	Intermediate Similarity	NPC471125
0.7563	Intermediate Similarity	NPC284707
0.7563	Intermediate Similarity	NPC159928
0.7563	Intermediate Similarity	NPC472758
0.7563	Intermediate Similarity	NPC473720
0.7563	Intermediate Similarity	NPC171905
0.7561	Intermediate Similarity	NPC471939
0.7561	Intermediate Similarity	NPC181999
0.7547	Intermediate Similarity	NPC49420
0.7547	Intermediate Similarity	NPC20713

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 NPC473975 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	2145
0.2-0.3	3864
0.3-0.4	1951
0.4-0.5	614
0.5-0.6	248
0.6-0.7	82
0.7-0.8	6
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
0.7928	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6648	Approved
0.7321	Intermediate Similarity	NPD5344	Discontinued
0.7241	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4225	Approved
0.7049	Intermediate Similarity	NPD7115	Discovery
0.6972	Remote Similarity	NPD6698	Approved
0.6972	Remote Similarity	NPD46	Approved
0.6923	Remote Similarity	NPD6008	Approved
0.6833	Remote Similarity	NPD6371	Approved
0.6807	Remote Similarity	NPD6686	Approved
0.6746	Remote Similarity	NPD6319	Approved
0.6727	Remote Similarity	NPD1695	Approved
0.6718	Remote Similarity	NPD7319	Approved
0.6696	Remote Similarity	NPD7638	Approved
0.6693	Remote Similarity	NPD6921	Approved
0.6667	Remote Similarity	NPD7492	Approved
0.664	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7640	Approved
0.6638	Remote Similarity	NPD7639	Approved
0.6637	Remote Similarity	NPD5282	Discontinued
0.6615	Remote Similarity	NPD6616	Approved
0.6614	Remote Similarity	NPD6059	Approved
0.6614	Remote Similarity	NPD6054	Approved
0.6612	Remote Similarity	NPD6372	Approved
0.6612	Remote Similarity	NPD6373	Approved
0.6589	Remote Similarity	NPD8328	Phase 3
0.6585	Remote Similarity	NPD8297	Approved
0.6581	Remote Similarity	NPD1700	Approved
0.6565	Remote Similarity	NPD8293	Discontinued
0.6565	Remote Similarity	NPD7078	Approved
0.6562	Remote Similarity	NPD8513	Phase 3
0.6562	Remote Similarity	NPD8516	Approved
0.6562	Remote Similarity	NPD8517	Approved
0.6562	Remote Similarity	NPD8515	Approved
0.6542	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD3168	Discontinued
0.6515	Remote Similarity	NPD7736	Approved
0.6514	Remote Similarity	NPD1694	Approved
0.6512	Remote Similarity	NPD6370	Approved
0.6504	Remote Similarity	NPD6649	Approved
0.6504	Remote Similarity	NPD6650	Approved
0.65	Remote Similarity	NPD5739	Approved
0.65	Remote Similarity	NPD6402	Approved
0.65	Remote Similarity	NPD7128	Approved
0.65	Remote Similarity	NPD6675	Approved
0.6489	Remote Similarity	NPD7507	Approved
0.646	Remote Similarity	NPD7983	Approved
0.6457	Remote Similarity	NPD7327	Approved
0.6457	Remote Similarity	NPD7328	Approved
0.6434	Remote Similarity	NPD6015	Approved
0.6434	Remote Similarity	NPD6016	Approved
0.6406	Remote Similarity	NPD7516	Approved
0.6404	Remote Similarity	NPD6399	Phase 3
0.6404	Remote Similarity	NPD5778	Approved
0.6404	Remote Similarity	NPD5779	Approved
0.6393	Remote Similarity	NPD7320	Approved
0.6393	Remote Similarity	NPD6899	Approved
0.6393	Remote Similarity	NPD6881	Approved
0.6385	Remote Similarity	NPD5988	Approved
0.6372	Remote Similarity	NPD7838	Discovery
0.6348	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7900	Approved
0.6339	Remote Similarity	NPD5737	Approved
0.6339	Remote Similarity	NPD6672	Approved
0.6336	Remote Similarity	NPD7604	Phase 2
0.632	Remote Similarity	NPD6882	Approved
0.6316	Remote Similarity	NPD7637	Suspended
0.6316	Remote Similarity	NPD8074	Phase 3
0.6316	Remote Similarity	NPD5693	Phase 1
0.6311	Remote Similarity	NPD5697	Approved
0.6311	Remote Similarity	NPD5701	Approved
0.6293	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7102	Approved
0.629	Remote Similarity	NPD6883	Approved
0.629	Remote Similarity	NPD7290	Approved
0.627	Remote Similarity	NPD8133	Approved
0.627	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6009	Approved
0.624	Remote Similarity	NPD8130	Phase 1
0.624	Remote Similarity	NPD6847	Approved
0.624	Remote Similarity	NPD6617	Approved
0.624	Remote Similarity	NPD6869	Approved
0.621	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.621	Remote Similarity	NPD6012	Approved
0.621	Remote Similarity	NPD6014	Approved
0.621	Remote Similarity	NPD6013	Approved
0.6186	Remote Similarity	NPD6083	Phase 2
0.6186	Remote Similarity	NPD7902	Approved
0.6186	Remote Similarity	NPD6084	Phase 2
0.6183	Remote Similarity	NPD8033	Approved
0.6183	Remote Similarity	NPD8296	Approved
0.6183	Remote Similarity	NPD8335	Approved
0.6183	Remote Similarity	NPD8380	Approved
0.6183	Remote Similarity	NPD5983	Phase 2
0.6183	Remote Similarity	NPD8379	Approved
0.6183	Remote Similarity	NPD8378	Approved
0.6174	Remote Similarity	NPD6411	Approved
0.6161	Remote Similarity	NPD6098	Approved
0.6154	Remote Similarity	NPD5695	Phase 3
0.6148	Remote Similarity	NPD6033	Approved
0.614	Remote Similarity	NPD6080	Approved
0.614	Remote Similarity	NPD6904	Approved
0.614	Remote Similarity	NPD6673	Approved
0.6134	Remote Similarity	NPD5696	Approved
0.6131	Remote Similarity	NPD7260	Phase 2
0.6129	Remote Similarity	NPD6011	Approved
0.6119	Remote Similarity	NPD6336	Discontinued
0.6116	Remote Similarity	NPD7632	Discontinued
0.6111	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD8377	Approved
0.6107	Remote Similarity	NPD8294	Approved
0.6087	Remote Similarity	NPD5785	Approved
0.6068	Remote Similarity	NPD6001	Approved
0.6068	Remote Similarity	NPD7748	Approved
0.6063	Remote Similarity	NPD6053	Discontinued
0.6038	Remote Similarity	NPD8039	Approved
0.6034	Remote Similarity	NPD6050	Approved
0.6034	Remote Similarity	NPD8035	Phase 2
0.6034	Remote Similarity	NPD8034	Phase 2
0.6032	Remote Similarity	NPD4634	Approved
0.6028	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD7521	Approved
0.6018	Remote Similarity	NPD6409	Approved
0.6018	Remote Similarity	NPD7334	Approved
0.6018	Remote Similarity	NPD6684	Approved
0.6018	Remote Similarity	NPD7146	Approved
0.6018	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6101	Approved
0.5971	Remote Similarity	NPD6845	Suspended
0.5968	Remote Similarity	NPD5357	Phase 1
0.5948	Remote Similarity	NPD5692	Phase 3
0.5946	Remote Similarity	NPD5209	Approved
0.594	Remote Similarity	NPD7503	Approved
0.5923	Remote Similarity	NPD6274	Approved
0.592	Remote Similarity	NPD6412	Phase 2
0.5917	Remote Similarity	NPD4755	Approved
0.5913	Remote Similarity	NPD6903	Approved
0.5913	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7100	Approved
0.5909	Remote Similarity	NPD7101	Approved
0.5897	Remote Similarity	NPD7515	Phase 2
0.5897	Remote Similarity	NPD5694	Approved
0.5882	Remote Similarity	NPD8273	Phase 1
0.5856	Remote Similarity	NPD5369	Approved
0.5854	Remote Similarity	NPD5211	Phase 2
0.5841	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6335	Approved
0.5833	Remote Similarity	NPD7839	Suspended
0.5826	Remote Similarity	NPD3573	Approved
0.5826	Remote Similarity	NPD4250	Approved
0.5826	Remote Similarity	NPD4251	Approved
0.5826	Remote Similarity	NPD7524	Approved
0.5821	Remote Similarity	NPD6908	Approved
0.5821	Remote Similarity	NPD6909	Approved
0.582	Remote Similarity	NPD4696	Approved
0.582	Remote Similarity	NPD5285	Approved
0.582	Remote Similarity	NPD4700	Approved
0.582	Remote Similarity	NPD5286	Approved
0.5804	Remote Similarity	NPD4269	Approved
0.5804	Remote Similarity	NPD4270	Approved
0.576	Remote Similarity	NPD5141	Approved
0.5758	Remote Similarity	NPD6317	Approved
0.5752	Remote Similarity	NPD7154	Phase 3
0.5752	Remote Similarity	NPD6695	Phase 3
0.5739	Remote Similarity	NPD3618	Phase 1
0.5739	Remote Similarity	NPD5786	Approved
0.5739	Remote Similarity	NPD4249	Approved
0.5735	Remote Similarity	NPD7642	Approved
0.5734	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD5226	Approved
0.5726	Remote Similarity	NPD5225	Approved
0.5726	Remote Similarity	NPD5224	Approved
0.5726	Remote Similarity	NPD4633	Approved
0.5714	Remote Similarity	NPD5956	Approved
0.5714	Remote Similarity	NPD6314	Approved
0.5714	Remote Similarity	NPD4767	Approved
0.5714	Remote Similarity	NPD4768	Approved
0.5714	Remote Similarity	NPD6313	Approved
0.5704	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD4786	Approved
0.5702	Remote Similarity	NPD3668	Phase 3
0.5702	Remote Similarity	NPD4697	Phase 3
0.5682	Remote Similarity	NPD6868	Approved
0.568	Remote Similarity	NPD5175	Approved
0.568	Remote Similarity	NPD5174	Approved
0.5678	Remote Similarity	NPD5207	Approved
0.5664	Remote Similarity	NPD8415	Approved
0.5664	Remote Similarity	NPD3667	Approved
0.5659	Remote Similarity	NPD2067	Discontinued

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