NPASS Compound

Structure

NPC475587 OpenBabel07101719252D 39 42 0 0 1 0 0 0 0 0999 V2000 -3.2779 2.8590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5031 0.1153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3489 -0.3731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 5.8201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1948 4.0223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1088 -1.8867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0036 1.8313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7763 -1.4626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7748 3.3474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 3.6492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3489 1.5804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3489 2.5571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3489 2.5571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5031 1.0920 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1948 0.1153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2599 5.0299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3489 4.5106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1374 -1.7846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3489 1.5804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0831 3.3474 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5031 3.0455 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7748 0.7902 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6572 1.5804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0831 0.7902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7748 -0.7902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6572 2.5571 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8459 -0.4884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8459 0.4884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0407 -0.3731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7115 5.1320 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3489 5.4874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4367 -2.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0767 -1.7191 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1948 1.0920 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6572 4.1376 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5031 4.0223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6572 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3489 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 8 27 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 20 1 0 0 0 0 11 13 2 0 0 0 0 11 22 1 0 0 0 0 12 19 1 0 0 0 0 12 21 1 0 0 0 0 14 2 1 6 0 0 0 14 19 1 0 0 0 0 14 23 1 0 0 0 0 15 29 2 0 0 0 0 15 34 1 0 0 0 0 16 30 2 0 0 0 0 16 35 1 0 0 0 0 17 31 2 0 0 0 0 17 36 1 0 0 0 0 18 32 2 0 0 0 0 18 37 1 0 0 0 0 19 34 1 6 0 0 0 20 26 1 1 0 0 0 20 35 1 0 0 0 0 21 26 1 1 0 0 0 21 36 1 0 0 0 0 22 28 1 1 0 0 0 22 38 1 0 0 0 0 23 24 1 0 0 0 0 23 26 1 6 0 0 0 24 28 1 1 0 0 0 24 37 1 0 0 0 0 25 27 1 0 0 0 0 25 33 2 0 0 0 0 25 38 1 0 0 0 0 26 7 1 6 0 0 0 27 28 1 6 0 0 0 27 39 1 0 0 0 0 28 39 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	550.24
Volume:	539.492
LogP:	2.64
LogD:	2.338
LogS:	-4.387
# Rotatable Bonds:	8
TPSA:	144.03
# H-Bond Aceptor:	11
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.22
Synthetic Accessibility Score:	6.028
Fsp3:	0.75
Lipinski Rule-of-5:	Rejected
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:	-5.15
MDCK Permeability:	0.00016033551946748048
Pgp-inhibitor:	0.999
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.264
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.63
Plasma Protein Binding (PPB):	59.13495635986328%
Volume Distribution (VD):	1.736
Pgp-substrate:	37.03569030761719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.024
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.19
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.337
CYP3A4-substrate:	0.444

ADMET: Excretion

Clearance (CL):	3.459
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.971
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.162
Rat Oral Acute Toxicity:	0.307
Maximum Recommended Daily Dose:	0.046
Skin Sensitization:	0.406
Carcinogencity:	0.109
Eye Corrosion:	0.059
Eye Irritation:	0.085
Respiratory Toxicity:	0.879

Download Data

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

Natural Product: NPC475587

Natural Product ID:	NPC475587
*Common Name:**	Excavatolide G
IUPAC Name:	n.a.
Synonyms:	Excavatolide G
Standard InCHIKey:	WRYYYJGXEFMEDX-HKOMCPJHSA-N
Standard InCHI:	InChI=1S/C28H38O11/c1-13-9-10-20(35-16(4)30)26(7)21(36-17(5)31)12-19(34-15(3)29)14(2)23(26)24(37-18(6)32)28-22(11-13)38-25(33)27(28,8)39-28/h11,14,19-24H,9-10,12H2,1-8H3/b13-11-/t14-,19-,20+,21-,22-,23+,24+,26-,27-,28-/m0/s1
SMILES:	CC1C(CC(C2(C1C(C34C(C=C(CCC2OC(=O)C)C)OC(=O)C3(O4)C)OC(=O)C)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508718
PubChem CID:	10602746
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
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096858]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10543904]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277747]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11720523]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599257]
NPO4817	Briareum excavatum	Species	Briareidae	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
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	=	15.7	ug ml-1	PMID[485016]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[485016]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	22.8	ug ml-1	PMID[485016]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[485016]

☑ 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 NPC475587 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	262
0.1-0.2	1528
0.2-0.3	4878
0.3-0.4	8690
0.4-0.5	13491
0.5-0.6	7558
0.6-0.7	5050
0.7-0.8	1150
0.8-0.85	45
0.85-0.9	21
0.9-0.95	9
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475510
0.9899	High Similarity	NPC473595
0.9899	High Similarity	NPC473939
0.9703	High Similarity	NPC474586
0.9703	High Similarity	NPC473594
0.9703	High Similarity	NPC473843
0.9703	High Similarity	NPC281624
0.9703	High Similarity	NPC473975
0.9608	High Similarity	NPC194619
0.9515	High Similarity	NPC473877
0.9495	High Similarity	NPC19239
0.9495	High Similarity	NPC474166
0.9245	High Similarity	NPC474333
0.9223	High Similarity	NPC42662
0.9159	High Similarity	NPC296822
0.9126	High Similarity	NPC94377
0.9038	High Similarity	NPC475922
0.8952	High Similarity	NPC161816
0.8952	High Similarity	NPC115257
0.8889	High Similarity	NPC476710
0.8889	High Similarity	NPC476711
0.8807	High Similarity	NPC476713
0.8807	High Similarity	NPC476712
0.8796	High Similarity	NPC73314
0.875	High Similarity	NPC9303
0.875	High Similarity	NPC475802
0.875	High Similarity	NPC16313
0.8667	High Similarity	NPC324327
0.8667	High Similarity	NPC326994
0.8667	High Similarity	NPC474421
0.8667	High Similarity	NPC194620
0.8667	High Similarity	NPC72813
0.8641	High Similarity	NPC183571
0.8585	High Similarity	NPC169888
0.8585	High Similarity	NPC55972
0.8585	High Similarity	NPC233379
0.8585	High Similarity	NPC14862
0.8585	High Similarity	NPC474664
0.8585	High Similarity	NPC327286
0.8558	High Similarity	NPC69171
0.8558	High Similarity	NPC474165
0.8545	High Similarity	NPC477509
0.8532	High Similarity	NPC477126
0.8505	High Similarity	NPC15218
0.8482	Intermediate Similarity	NPC470186
0.8476	Intermediate Similarity	NPC477127
0.8431	Intermediate Similarity	NPC471140
0.8381	Intermediate Similarity	NPC4620
0.8378	Intermediate Similarity	NPC270478
0.8365	Intermediate Similarity	NPC476478
0.8318	Intermediate Similarity	NPC474716
0.8302	Intermediate Similarity	NPC475676
0.8302	Intermediate Similarity	NPC220964
0.8273	Intermediate Similarity	NPC317687
0.8273	Intermediate Similarity	NPC471933
0.8261	Intermediate Similarity	NPC282003
0.8261	Intermediate Similarity	NPC188222
0.8261	Intermediate Similarity	NPC310035
0.8224	Intermediate Similarity	NPC470975
0.8224	Intermediate Similarity	NPC103088
0.8224	Intermediate Similarity	NPC470979
0.819	Intermediate Similarity	NPC264477
0.819	Intermediate Similarity	NPC303006
0.819	Intermediate Similarity	NPC477511
0.819	Intermediate Similarity	NPC98225
0.8182	Intermediate Similarity	NPC317107
0.8173	Intermediate Similarity	NPC264378
0.8165	Intermediate Similarity	NPC469370
0.8165	Intermediate Similarity	NPC471934
0.8155	Intermediate Similarity	NPC17585
0.8148	Intermediate Similarity	NPC180744
0.8142	Intermediate Similarity	NPC473590
0.8137	Intermediate Similarity	NPC161998
0.81	Intermediate Similarity	NPC475971
0.8091	Intermediate Similarity	NPC253906
0.8087	Intermediate Similarity	NPC475003
0.8073	Intermediate Similarity	NPC322903
0.8034	Intermediate Similarity	NPC67251
0.8019	Intermediate Similarity	NPC474339
0.8019	Intermediate Similarity	NPC164598
0.8017	Intermediate Similarity	NPC470185
0.7982	Intermediate Similarity	NPC469684
0.7982	Intermediate Similarity	NPC469558
0.7963	Intermediate Similarity	NPC471143
0.7963	Intermediate Similarity	NPC477510
0.7944	Intermediate Similarity	NPC474709
0.7944	Intermediate Similarity	NPC471148
0.7928	Intermediate Similarity	NPC475563
0.7928	Intermediate Similarity	NPC475134
0.7928	Intermediate Similarity	NPC472214
0.7928	Intermediate Similarity	NPC472215
0.7925	Intermediate Similarity	NPC477512
0.7925	Intermediate Similarity	NPC469551
0.7913	Intermediate Similarity	NPC470776
0.7909	Intermediate Similarity	NPC476479
0.79	Intermediate Similarity	NPC266957
0.7895	Intermediate Similarity	NPC470793
0.7895	Intermediate Similarity	NPC474734
0.789	Intermediate Similarity	NPC284365
0.789	Intermediate Similarity	NPC123726
0.7881	Intermediate Similarity	NPC105926
0.7881	Intermediate Similarity	NPC472399
0.7881	Intermediate Similarity	NPC265557
0.7881	Intermediate Similarity	NPC18945
0.7881	Intermediate Similarity	NPC91693
0.7876	Intermediate Similarity	NPC89018
0.7876	Intermediate Similarity	NPC33360
0.7876	Intermediate Similarity	NPC470120
0.7876	Intermediate Similarity	NPC159333
0.7864	Intermediate Similarity	NPC476597
0.7864	Intermediate Similarity	NPC476598
0.7863	Intermediate Similarity	NPC470779
0.7857	Intermediate Similarity	NPC469656
0.7857	Intermediate Similarity	NPC474846
0.7857	Intermediate Similarity	NPC475668
0.7857	Intermediate Similarity	NPC473921
0.7857	Intermediate Similarity	NPC470467
0.7857	Intermediate Similarity	NPC475480
0.7857	Intermediate Similarity	NPC469655
0.7845	Intermediate Similarity	NPC475520
0.7843	Intermediate Similarity	NPC475748
0.7838	Intermediate Similarity	NPC475191
0.7826	Intermediate Similarity	NPC176513
0.7826	Intermediate Similarity	NPC470775
0.7826	Intermediate Similarity	NPC98249
0.7826	Intermediate Similarity	NPC53396
0.7826	Intermediate Similarity	NPC58662
0.7818	Intermediate Similarity	NPC67321
0.7818	Intermediate Similarity	NPC477513
0.7818	Intermediate Similarity	NPC187435
0.7815	Intermediate Similarity	NPC24651
0.7815	Intermediate Similarity	NPC476729
0.7807	Intermediate Similarity	NPC88867
0.7807	Intermediate Similarity	NPC226608
0.78	Intermediate Similarity	NPC50637
0.7798	Intermediate Similarity	NPC258532
0.7798	Intermediate Similarity	NPC146731
0.7797	Intermediate Similarity	NPC312833
0.7788	Intermediate Similarity	NPC476596
0.7788	Intermediate Similarity	NPC222834
0.7788	Intermediate Similarity	NPC471147
0.7788	Intermediate Similarity	NPC470468
0.7788	Intermediate Similarity	NPC269530
0.7778	Intermediate Similarity	NPC105725
0.7778	Intermediate Similarity	NPC4548
0.7778	Intermediate Similarity	NPC157252
0.7778	Intermediate Similarity	NPC471128
0.7778	Intermediate Similarity	NPC145182
0.7778	Intermediate Similarity	NPC471126
0.7778	Intermediate Similarity	NPC476081
0.7767	Intermediate Similarity	NPC233437
0.7767	Intermediate Similarity	NPC207641
0.7767	Intermediate Similarity	NPC20713
0.7767	Intermediate Similarity	NPC49420
0.7759	Intermediate Similarity	NPC473720
0.7759	Intermediate Similarity	NPC284707
0.7757	Intermediate Similarity	NPC475949
0.7757	Intermediate Similarity	NPC474718
0.775	Intermediate Similarity	NPC181999
0.7745	Intermediate Similarity	NPC151770
0.7739	Intermediate Similarity	NPC470466
0.7736	Intermediate Similarity	NPC100912
0.7736	Intermediate Similarity	NPC474921
0.7731	Intermediate Similarity	NPC473802
0.7719	Intermediate Similarity	NPC473535
0.7719	Intermediate Similarity	NPC94509
0.7714	Intermediate Similarity	NPC475659
0.7712	Intermediate Similarity	NPC472401
0.7712	Intermediate Similarity	NPC52839
0.7705	Intermediate Similarity	NPC476851
0.7699	Intermediate Similarity	NPC157476
0.7699	Intermediate Similarity	NPC475495
0.7692	Intermediate Similarity	NPC472667
0.7692	Intermediate Similarity	NPC312536
0.7686	Intermediate Similarity	NPC470780
0.7685	Intermediate Similarity	NPC308824
0.7679	Intermediate Similarity	NPC273433
0.7679	Intermediate Similarity	NPC474242
0.7679	Intermediate Similarity	NPC87335
0.7677	Intermediate Similarity	NPC222358
0.7672	Intermediate Similarity	NPC478204
0.7672	Intermediate Similarity	NPC473656
0.767	Intermediate Similarity	NPC475776
0.7667	Intermediate Similarity	NPC473709
0.7667	Intermediate Similarity	NPC470922
0.7667	Intermediate Similarity	NPC473919
0.7664	Intermediate Similarity	NPC471932
0.7664	Intermediate Similarity	NPC107806
0.7664	Intermediate Similarity	NPC216478
0.7664	Intermediate Similarity	NPC208233
0.7664	Intermediate Similarity	NPC72647
0.7658	Intermediate Similarity	NPC143609
0.7652	Intermediate Similarity	NPC473798
0.7647	Intermediate Similarity	NPC23786
0.7647	Intermediate Similarity	NPC477128
0.7647	Intermediate Similarity	NPC470265
0.7647	Intermediate Similarity	NPC19464
0.7647	Intermediate Similarity	NPC162009
0.7647	Intermediate Similarity	NPC257017
0.7642	Intermediate Similarity	NPC230800

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 NPC475587 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	1971
0.2-0.3	3819
0.3-0.4	2051
0.4-0.5	680
0.5-0.6	285
0.6-0.7	118
0.7-0.8	8
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
0.7658	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD4225	Approved
0.7281	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD7115	Discovery
0.7217	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD46	Approved
0.717	Intermediate Similarity	NPD6698	Approved
0.7117	Intermediate Similarity	NPD6648	Approved
0.7105	Intermediate Similarity	NPD6008	Approved
0.7054	Intermediate Similarity	NPD5344	Discontinued
0.7009	Intermediate Similarity	NPD6371	Approved
0.6983	Remote Similarity	NPD6686	Approved
0.6916	Remote Similarity	NPD1695	Approved
0.6911	Remote Similarity	NPD6319	Approved
0.6875	Remote Similarity	NPD7638	Approved
0.6875	Remote Similarity	NPD7319	Approved
0.6825	Remote Similarity	NPD7492	Approved
0.6818	Remote Similarity	NPD5282	Discontinued
0.6814	Remote Similarity	NPD7639	Approved
0.6814	Remote Similarity	NPD7640	Approved
0.6807	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6372	Approved
0.678	Remote Similarity	NPD6373	Approved
0.6774	Remote Similarity	NPD6059	Approved
0.6774	Remote Similarity	NPD6054	Approved
0.6772	Remote Similarity	NPD6616	Approved
0.675	Remote Similarity	NPD8297	Approved
0.6746	Remote Similarity	NPD8328	Phase 3
0.6731	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8517	Approved
0.672	Remote Similarity	NPD8516	Approved
0.672	Remote Similarity	NPD8515	Approved
0.672	Remote Similarity	NPD8513	Phase 3
0.672	Remote Similarity	NPD6921	Approved
0.6719	Remote Similarity	NPD8293	Discontinued
0.6719	Remote Similarity	NPD7078	Approved
0.6698	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6641	Remote Similarity	NPD7507	Approved
0.6636	Remote Similarity	NPD7983	Approved
0.6609	Remote Similarity	NPD1700	Approved
0.6587	Remote Similarity	NPD6015	Approved
0.6587	Remote Similarity	NPD6016	Approved
0.6577	Remote Similarity	NPD5778	Approved
0.6577	Remote Similarity	NPD5779	Approved
0.6577	Remote Similarity	NPD6399	Phase 3
0.6555	Remote Similarity	NPD6881	Approved
0.6555	Remote Similarity	NPD7320	Approved
0.6555	Remote Similarity	NPD6899	Approved
0.6545	Remote Similarity	NPD7838	Discovery
0.6535	Remote Similarity	NPD5988	Approved
0.6518	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7900	Approved
0.6514	Remote Similarity	NPD6672	Approved
0.6514	Remote Similarity	NPD5737	Approved
0.6486	Remote Similarity	NPD5693	Phase 1
0.6486	Remote Similarity	NPD7637	Suspended
0.6484	Remote Similarity	NPD7604	Phase 2
0.648	Remote Similarity	NPD7328	Approved
0.648	Remote Similarity	NPD7327	Approved
0.6475	Remote Similarity	NPD6882	Approved
0.6471	Remote Similarity	NPD5697	Approved
0.6471	Remote Similarity	NPD5701	Approved
0.6462	Remote Similarity	NPD8074	Phase 3
0.646	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.646	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6883	Approved
0.6446	Remote Similarity	NPD7290	Approved
0.6446	Remote Similarity	NPD7102	Approved
0.6429	Remote Similarity	NPD7516	Approved
0.6423	Remote Similarity	NPD8133	Approved
0.6423	Remote Similarity	NPD4632	Approved
0.64	Remote Similarity	NPD6009	Approved
0.6393	Remote Similarity	NPD6617	Approved
0.6393	Remote Similarity	NPD8130	Phase 1
0.6393	Remote Similarity	NPD6869	Approved
0.6393	Remote Similarity	NPD6847	Approved
0.6364	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6014	Approved
0.6364	Remote Similarity	NPD6012	Approved
0.6364	Remote Similarity	NPD6013	Approved
0.6348	Remote Similarity	NPD6083	Phase 2
0.6348	Remote Similarity	NPD7902	Approved
0.6348	Remote Similarity	NPD6084	Phase 2
0.6339	Remote Similarity	NPD6411	Approved
0.633	Remote Similarity	NPD6098	Approved
0.6328	Remote Similarity	NPD8335	Approved
0.6328	Remote Similarity	NPD8379	Approved
0.6328	Remote Similarity	NPD8033	Approved
0.6328	Remote Similarity	NPD8378	Approved
0.6328	Remote Similarity	NPD5983	Phase 2
0.6328	Remote Similarity	NPD8296	Approved
0.6328	Remote Similarity	NPD8380	Approved
0.6316	Remote Similarity	NPD5695	Phase 3
0.6306	Remote Similarity	NPD6904	Approved
0.6306	Remote Similarity	NPD6673	Approved
0.6306	Remote Similarity	NPD6080	Approved
0.6293	Remote Similarity	NPD5696	Approved
0.6288	Remote Similarity	NPD6033	Approved
0.6281	Remote Similarity	NPD6011	Approved
0.6271	Remote Similarity	NPD7632	Discontinued
0.6269	Remote Similarity	NPD7260	Phase 2
0.626	Remote Similarity	NPD6336	Discontinued
0.626	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5785	Approved
0.625	Remote Similarity	NPD8294	Approved
0.625	Remote Similarity	NPD3168	Discontinued
0.625	Remote Similarity	NPD8377	Approved
0.6228	Remote Similarity	NPD7748	Approved
0.6214	Remote Similarity	NPD8039	Approved
0.621	Remote Similarity	NPD6053	Discontinued
0.6195	Remote Similarity	NPD8035	Phase 2
0.6195	Remote Similarity	NPD6050	Approved
0.6195	Remote Similarity	NPD8034	Phase 2
0.6182	Remote Similarity	NPD7334	Approved
0.6182	Remote Similarity	NPD6684	Approved
0.6182	Remote Similarity	NPD7146	Approved
0.6182	Remote Similarity	NPD6409	Approved
0.6182	Remote Similarity	NPD5330	Approved
0.6182	Remote Similarity	NPD7521	Approved
0.6179	Remote Similarity	NPD4634	Approved
0.6161	Remote Similarity	NPD6101	Approved
0.6161	Remote Similarity	NPD6051	Approved
0.6161	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5209	Approved
0.6106	Remote Similarity	NPD5692	Phase 3
0.6103	Remote Similarity	NPD6845	Suspended
0.6087	Remote Similarity	NPD6001	Approved
0.6077	Remote Similarity	NPD7503	Approved
0.6071	Remote Similarity	NPD6903	Approved
0.6071	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD4755	Approved
0.6066	Remote Similarity	NPD6412	Phase 2
0.6063	Remote Similarity	NPD6274	Approved
0.6053	Remote Similarity	NPD5694	Approved
0.6053	Remote Similarity	NPD7515	Phase 2
0.6047	Remote Similarity	NPD7101	Approved
0.6047	Remote Similarity	NPD7100	Approved
0.6019	Remote Similarity	NPD5369	Approved
0.6015	Remote Similarity	NPD8273	Phase 1
0.6	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD7839	Suspended
0.5982	Remote Similarity	NPD7524	Approved
0.5982	Remote Similarity	NPD4251	Approved
0.5982	Remote Similarity	NPD3573	Approved
0.5982	Remote Similarity	NPD4250	Approved
0.5969	Remote Similarity	NPD6335	Approved
0.5966	Remote Similarity	NPD5286	Approved
0.5966	Remote Similarity	NPD4696	Approved
0.5966	Remote Similarity	NPD4700	Approved
0.5966	Remote Similarity	NPD5285	Approved
0.5963	Remote Similarity	NPD4269	Approved
0.5963	Remote Similarity	NPD4270	Approved
0.5954	Remote Similarity	NPD6908	Approved
0.5954	Remote Similarity	NPD6909	Approved
0.5909	Remote Similarity	NPD6695	Phase 3
0.5909	Remote Similarity	NPD7154	Phase 3
0.5902	Remote Similarity	NPD5141	Approved
0.5893	Remote Similarity	NPD4249	Approved
0.5893	Remote Similarity	NPD5786	Approved
0.5893	Remote Similarity	NPD3618	Phase 1
0.5891	Remote Similarity	NPD6317	Approved
0.5868	Remote Similarity	NPD5224	Approved
0.5868	Remote Similarity	NPD4633	Approved
0.5868	Remote Similarity	NPD5226	Approved
0.5868	Remote Similarity	NPD5225	Approved
0.5865	Remote Similarity	NPD7642	Approved
0.5857	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD3668	Phase 3
0.5856	Remote Similarity	NPD4786	Approved
0.5854	Remote Similarity	NPD4767	Approved
0.5854	Remote Similarity	NPD4768	Approved
0.5847	Remote Similarity	NPD4697	Phase 3
0.5846	Remote Similarity	NPD6313	Approved
0.5846	Remote Similarity	NPD6314	Approved
0.5839	Remote Similarity	NPD5956	Approved
0.5833	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD5207	Approved
0.582	Remote Similarity	NPD5175	Approved
0.582	Remote Similarity	NPD5174	Approved
0.5818	Remote Similarity	NPD3667	Approved
0.5814	Remote Similarity	NPD6868	Approved
0.5804	Remote Similarity	NPD5363	Approved
0.5804	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD6082	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