NPASS Compound

Structure

NPC19907 OpenBabel07101719512D 23 24 0 0 1 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 14 2 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 13 21 2 0 0 0 0 14 19 1 0 0 0 0 15 20 1 6 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	353.188
LogP:	3.854
LogD:	2.674
LogS:	-4.092
# Rotatable Bonds:	5
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.451
Synthetic Accessibility Score:	4.53
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.181
MDCK Permeability:	2.104727718688082e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	94.76873016357422%
Volume Distribution (VD):	0.375
Pgp-substrate:	5.682413101196289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.418
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.126
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.385
CYP3A4-inhibitor:	0.144
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	2.41
Half-life (T1/2):	0.849

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.214
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.549
Skin Sensitization:	0.963
Carcinogencity:	0.097
Eye Corrosion:	0.988
Eye Irritation:	0.971
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC19907

Natural Product ID:	NPC19907
*Common Name:**	16-Oxo-Cleroda-3,13-Dien-15-Oic Acid
IUPAC Name:	(E)-5-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-formylpent-2-enoic acid
Synonyms:
Standard InCHIKey:	LUZARHTWSOXFLP-HEZUFYQYSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-14-6-5-7-17-19(14,3)10-8-15(2)20(17,4)11-9-16(13-21)12-18(22)23/h6,12-13,15,17H,5,7-11H2,1-4H3,(H,22,23)/p-1/b16-12+/t15-,17+,19+,20+/m1/s1
SMILES:	CC1=CCC[C@H]2[C@@]1(C)CC[C@@H](C)[C@]2(C)CC/C(=CC(=O)[O-])/C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079774
PubChem CID:	38355304
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087586]
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19860383]
NPO30067	Polyalthia longifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21872367]
NPO30067	Polyalthia longifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2292689]
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25747495]
NPO30067	Polyalthia longifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	2
MIC	2
Others	17

Activity Type	# Activity
Cell Line	2
Organism	19

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3700.0	nM	PMID[507912]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3100.0	nM	PMID[507912]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	20.0	ug.mL-1	PMID[507914]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MBC	=	185.0	ug ml-1	PMID[507914]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MBIC	=	20.0	ug ml-1	PMID[507914]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[507914]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	95.0	ug ml-1	PMID[507914]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBIC	=	16.0	ug ml-1	PMID[507914]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	<=	90.0	%	PMID[507914]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	Activity	<=	90.0	%	PMID[507914]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	7.5	log10CFU/ml	PMID[507914]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	Activity	=	7.5	log10CFU/ml	PMID[507914]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	9.0	log10CFU/ml	PMID[507914]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	TIME	>=	8.0	hr	PMID[507914]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	Ratio	=	5.0	n.a.	PMID[507914]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Ratio	=	5.0	n.a.	PMID[507914]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	Activity	=	92.06	%	PMID[507914]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	94.26	%	PMID[507914]

☑ 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 NPC19907 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	154
0.1-0.2	1454
0.2-0.3	7630
0.3-0.4	15547
0.4-0.5	8433
0.5-0.6	6310
0.6-0.7	2673
0.7-0.8	444
0.8-0.85	41
0.85-0.9	7
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9041	High Similarity	NPC476346
0.9028	High Similarity	NPC180015
0.9028	High Similarity	NPC56747
0.9028	High Similarity	NPC130016
0.9028	High Similarity	NPC109576
0.863	High Similarity	NPC133253
0.863	High Similarity	NPC21944
0.8592	High Similarity	NPC290350
0.8592	High Similarity	NPC4370
0.8472	Intermediate Similarity	NPC155198
0.8451	Intermediate Similarity	NPC259156
0.8451	Intermediate Similarity	NPC242945
0.8442	Intermediate Similarity	NPC59436
0.8289	Intermediate Similarity	NPC65650
0.8289	Intermediate Similarity	NPC476795
0.825	Intermediate Similarity	NPC472867
0.825	Intermediate Similarity	NPC142253
0.825	Intermediate Similarity	NPC3511
0.825	Intermediate Similarity	NPC472239
0.8205	Intermediate Similarity	NPC198240
0.8158	Intermediate Similarity	NPC168975
0.8158	Intermediate Similarity	NPC211641
0.8158	Intermediate Similarity	NPC75485
0.8158	Intermediate Similarity	NPC219232
0.8158	Intermediate Similarity	NPC128346
0.8158	Intermediate Similarity	NPC20025
0.8148	Intermediate Similarity	NPC97913
0.814	Intermediate Similarity	NPC151722
0.8133	Intermediate Similarity	NPC474562
0.8125	Intermediate Similarity	NPC90055
0.8077	Intermediate Similarity	NPC97377
0.8077	Intermediate Similarity	NPC61952
0.8072	Intermediate Similarity	NPC168248
0.8056	Intermediate Similarity	NPC107258
0.8049	Intermediate Similarity	NPC87552
0.8049	Intermediate Similarity	NPC472865
0.8049	Intermediate Similarity	NPC164577
0.8026	Intermediate Similarity	NPC35656
0.8025	Intermediate Similarity	NPC469799
0.8025	Intermediate Similarity	NPC469806
0.8025	Intermediate Similarity	NPC469804
0.8025	Intermediate Similarity	NPC469805
0.8	Intermediate Similarity	NPC472301
0.8	Intermediate Similarity	NPC469797
0.8	Intermediate Similarity	NPC271104
0.8	Intermediate Similarity	NPC469798
0.7975	Intermediate Similarity	NPC239098
0.7952	Intermediate Similarity	NPC70685
0.7952	Intermediate Similarity	NPC8571
0.7949	Intermediate Similarity	NPC180886
0.7945	Intermediate Similarity	NPC255781
0.7927	Intermediate Similarity	NPC118423
0.7927	Intermediate Similarity	NPC279639
0.7927	Intermediate Similarity	NPC3856
0.7927	Intermediate Similarity	NPC49019
0.7917	Intermediate Similarity	NPC52449
0.7917	Intermediate Similarity	NPC169275
0.7895	Intermediate Similarity	NPC160817
0.7882	Intermediate Similarity	NPC473229
0.7838	Intermediate Similarity	NPC193770
0.7831	Intermediate Similarity	NPC178025
0.7831	Intermediate Similarity	NPC472864
0.7831	Intermediate Similarity	NPC248758
0.7831	Intermediate Similarity	NPC19849
0.7831	Intermediate Similarity	NPC181743
0.7831	Intermediate Similarity	NPC16287
0.7821	Intermediate Similarity	NPC469803
0.7816	Intermediate Similarity	NPC476187
0.7805	Intermediate Similarity	NPC268122
0.7805	Intermediate Similarity	NPC142683
0.7792	Intermediate Similarity	NPC144947
0.7791	Intermediate Similarity	NPC472983
0.7791	Intermediate Similarity	NPC5509
0.775	Intermediate Similarity	NPC74410
0.775	Intermediate Similarity	NPC475994
0.775	Intermediate Similarity	NPC179028
0.775	Intermediate Similarity	NPC115515
0.775	Intermediate Similarity	NPC62336
0.7738	Intermediate Similarity	NPC86316
0.7738	Intermediate Similarity	NPC476426
0.7738	Intermediate Similarity	NPC189311
0.7738	Intermediate Similarity	NPC106416
0.7738	Intermediate Similarity	NPC65661
0.7738	Intermediate Similarity	NPC60350
0.7738	Intermediate Similarity	NPC2709
0.7733	Intermediate Similarity	NPC188292
0.7733	Intermediate Similarity	NPC260474
0.7727	Intermediate Similarity	NPC115021
0.7727	Intermediate Similarity	NPC469939
0.7722	Intermediate Similarity	NPC469793
0.7722	Intermediate Similarity	NPC263582
0.7722	Intermediate Similarity	NPC469796
0.7711	Intermediate Similarity	NPC215893
0.7711	Intermediate Similarity	NPC307258
0.7711	Intermediate Similarity	NPC41539
0.7711	Intermediate Similarity	NPC22611
0.7703	Intermediate Similarity	NPC81907
0.7701	Intermediate Similarity	NPC159748
0.7701	Intermediate Similarity	NPC101651
0.7692	Intermediate Similarity	NPC251970
0.7692	Intermediate Similarity	NPC476046
0.7692	Intermediate Similarity	NPC241854
0.7692	Intermediate Similarity	NPC213223
0.7683	Intermediate Similarity	NPC278459
0.7683	Intermediate Similarity	NPC40228
0.7674	Intermediate Similarity	NPC104560
0.7674	Intermediate Similarity	NPC72397
0.7674	Intermediate Similarity	NPC472870
0.7674	Intermediate Similarity	NPC48107
0.7662	Intermediate Similarity	NPC304983
0.7654	Intermediate Similarity	NPC327674
0.7654	Intermediate Similarity	NPC170793
0.7654	Intermediate Similarity	NPC308038
0.7654	Intermediate Similarity	NPC90965
0.7654	Intermediate Similarity	NPC152061
0.7647	Intermediate Similarity	NPC472869
0.7647	Intermediate Similarity	NPC82979
0.7647	Intermediate Similarity	NPC194417
0.7647	Intermediate Similarity	NPC186975
0.7647	Intermediate Similarity	NPC473226
0.7625	Intermediate Similarity	NPC165711
0.7625	Intermediate Similarity	NPC472300
0.7619	Intermediate Similarity	NPC165064
0.7619	Intermediate Similarity	NPC476412
0.7614	Intermediate Similarity	NPC230064
0.7614	Intermediate Similarity	NPC23217
0.7614	Intermediate Similarity	NPC179517
0.7614	Intermediate Similarity	NPC165904
0.7614	Intermediate Similarity	NPC470113
0.7609	Intermediate Similarity	NPC174314
0.7595	Intermediate Similarity	NPC279666
0.7595	Intermediate Similarity	NPC192540
0.7595	Intermediate Similarity	NPC472327
0.759	Intermediate Similarity	NPC94200
0.759	Intermediate Similarity	NPC200513
0.7586	Intermediate Similarity	NPC251528
0.7586	Intermediate Similarity	NPC66344
0.7586	Intermediate Similarity	NPC174342
0.7586	Intermediate Similarity	NPC118011
0.7586	Intermediate Similarity	NPC168131
0.7586	Intermediate Similarity	NPC36668
0.7568	Intermediate Similarity	NPC251118
0.7568	Intermediate Similarity	NPC268039
0.7561	Intermediate Similarity	NPC471514
0.7561	Intermediate Similarity	NPC474509
0.7558	Intermediate Similarity	NPC476293
0.7558	Intermediate Similarity	NPC476409
0.7558	Intermediate Similarity	NPC312561
0.7558	Intermediate Similarity	NPC236618
0.7532	Intermediate Similarity	NPC251929
0.7532	Intermediate Similarity	NPC235586
0.7532	Intermediate Similarity	NPC2634
0.7532	Intermediate Similarity	NPC265782
0.7531	Intermediate Similarity	NPC169095
0.7531	Intermediate Similarity	NPC275494
0.7531	Intermediate Similarity	NPC80088
0.7531	Intermediate Similarity	NPC321514
0.7531	Intermediate Similarity	NPC253561
0.7531	Intermediate Similarity	NPC471409
0.7529	Intermediate Similarity	NPC472940
0.7529	Intermediate Similarity	NPC255174
0.7529	Intermediate Similarity	NPC472931
0.7528	Intermediate Similarity	NPC242069
0.7528	Intermediate Similarity	NPC476416
0.75	Intermediate Similarity	NPC87141
0.75	Intermediate Similarity	NPC297398
0.75	Intermediate Similarity	NPC474976
0.75	Intermediate Similarity	NPC1254
0.75	Intermediate Similarity	NPC474790
0.75	Intermediate Similarity	NPC309399
0.75	Intermediate Similarity	NPC69143
0.75	Intermediate Similarity	NPC310992
0.75	Intermediate Similarity	NPC127582
0.75	Intermediate Similarity	NPC40353
0.7473	Intermediate Similarity	NPC472941
0.7473	Intermediate Similarity	NPC456
0.7471	Intermediate Similarity	NPC249889
0.7471	Intermediate Similarity	NPC193843
0.7471	Intermediate Similarity	NPC226863
0.7471	Intermediate Similarity	NPC117122
0.747	Intermediate Similarity	NPC14203
0.747	Intermediate Similarity	NPC116797
0.747	Intermediate Similarity	NPC4166
0.747	Intermediate Similarity	NPC6663
0.747	Intermediate Similarity	NPC327002
0.747	Intermediate Similarity	NPC229584
0.747	Intermediate Similarity	NPC471898
0.747	Intermediate Similarity	NPC477372
0.747	Intermediate Similarity	NPC473420
0.7468	Intermediate Similarity	NPC183503
0.7468	Intermediate Similarity	NPC283908
0.7468	Intermediate Similarity	NPC301065
0.7468	Intermediate Similarity	NPC161923
0.7468	Intermediate Similarity	NPC103958
0.7467	Intermediate Similarity	NPC185587
0.7442	Intermediate Similarity	NPC220478
0.7442	Intermediate Similarity	NPC322159
0.7442	Intermediate Similarity	NPC472974
0.7439	Intermediate Similarity	NPC19900
0.7436	Intermediate Similarity	NPC54123

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 NPC19907 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	1846
0.2-0.3	4263
0.3-0.4	2058
0.4-0.5	477
0.5-0.6	243
0.6-0.7	114
0.7-0.8	3
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
0.759	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4691	Approved
0.7403	Intermediate Similarity	NPD4137	Phase 3
0.7397	Intermediate Similarity	NPD4192	Approved
0.7397	Intermediate Similarity	NPD4191	Approved
0.7397	Intermediate Similarity	NPD4193	Approved
0.7397	Intermediate Similarity	NPD4194	Approved
0.7308	Intermediate Similarity	NPD4747	Approved
0.725	Intermediate Similarity	NPD4058	Approved
0.7045	Intermediate Similarity	NPD7146	Approved
0.7045	Intermediate Similarity	NPD7521	Approved
0.7045	Intermediate Similarity	NPD7334	Approved
0.7045	Intermediate Similarity	NPD6684	Approved
0.7045	Intermediate Similarity	NPD4623	Approved
0.7045	Intermediate Similarity	NPD5330	Approved
0.7045	Intermediate Similarity	NPD6409	Approved
0.7045	Intermediate Similarity	NPD4519	Discontinued
0.7037	Intermediate Similarity	NPD4687	Approved
0.7037	Intermediate Similarity	NPD5733	Approved
0.7033	Intermediate Similarity	NPD7515	Phase 2
0.7011	Intermediate Similarity	NPD3666	Approved
0.7011	Intermediate Similarity	NPD3133	Approved
0.7011	Intermediate Similarity	NPD3665	Phase 1
0.7	Intermediate Similarity	NPD5276	Approved
0.6941	Remote Similarity	NPD4695	Discontinued
0.6932	Remote Similarity	NPD1694	Approved
0.6889	Remote Similarity	NPD6903	Approved
0.6889	Remote Similarity	NPD6672	Approved
0.6889	Remote Similarity	NPD5737	Approved
0.6889	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7748	Approved
0.6875	Remote Similarity	NPD6404	Discontinued
0.6854	Remote Similarity	NPD3618	Phase 1
0.6835	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5695	Phase 3
0.6782	Remote Similarity	NPD4221	Approved
0.6782	Remote Similarity	NPD4223	Phase 3
0.6782	Remote Similarity	NPD3667	Approved
0.6778	Remote Similarity	NPD3573	Approved
0.6757	Remote Similarity	NPD287	Approved
0.6747	Remote Similarity	NPD8039	Approved
0.6706	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD6079	Approved
0.663	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5328	Approved
0.663	Remote Similarity	NPD4753	Phase 2
0.6629	Remote Similarity	NPD4197	Approved
0.6629	Remote Similarity	NPD4786	Approved
0.6598	Remote Similarity	NPD5696	Approved
0.6596	Remote Similarity	NPD6399	Phase 3
0.6562	Remote Similarity	NPD4697	Phase 3
0.6556	Remote Similarity	NPD5329	Approved
0.6538	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7640	Approved
0.6531	Remote Similarity	NPD7639	Approved
0.6526	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7900	Approved
0.6522	Remote Similarity	NPD5208	Approved
0.6517	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3617	Approved
0.6489	Remote Similarity	NPD5693	Phase 1
0.6486	Remote Similarity	NPD4219	Approved
0.6484	Remote Similarity	NPD5280	Approved
0.6484	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4689	Approved
0.6484	Remote Similarity	NPD4138	Approved
0.6484	Remote Similarity	NPD4693	Phase 3
0.6484	Remote Similarity	NPD4694	Approved
0.6484	Remote Similarity	NPD4688	Approved
0.6484	Remote Similarity	NPD4690	Approved
0.6484	Remote Similarity	NPD5205	Approved
0.6477	Remote Similarity	NPD8028	Phase 2
0.6458	Remote Similarity	NPD4629	Approved
0.6458	Remote Similarity	NPD5210	Approved
0.6452	Remote Similarity	NPD6673	Approved
0.6452	Remote Similarity	NPD6080	Approved
0.6452	Remote Similarity	NPD6904	Approved
0.6444	Remote Similarity	NPD3668	Phase 3
0.6429	Remote Similarity	NPD4225	Approved
0.6429	Remote Similarity	NPD7638	Approved
0.6421	Remote Similarity	NPD4202	Approved
0.64	Remote Similarity	NPD5211	Phase 2
0.6392	Remote Similarity	NPD7614	Phase 1
0.6392	Remote Similarity	NPD5222	Approved
0.6392	Remote Similarity	NPD5221	Approved
0.6392	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5692	Phase 3
0.6383	Remote Similarity	NPD5785	Approved
0.6383	Remote Similarity	NPD5207	Approved
0.6374	Remote Similarity	NPD5363	Approved
0.6374	Remote Similarity	NPD1696	Phase 3
0.6327	Remote Similarity	NPD5173	Approved
0.6316	Remote Similarity	NPD5694	Approved
0.6316	Remote Similarity	NPD6050	Approved
0.6311	Remote Similarity	NPD5697	Approved
0.6304	Remote Similarity	NPD6098	Approved
0.6289	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5141	Approved
0.6264	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD6686	Approved
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD6899	Approved
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD4195	Approved
0.625	Remote Similarity	NPD5778	Approved
0.6239	Remote Similarity	NPD7115	Discovery
0.6224	Remote Similarity	NPD7732	Phase 3
0.6214	Remote Similarity	NPD6675	Approved
0.6214	Remote Similarity	NPD7128	Approved
0.6214	Remote Similarity	NPD5739	Approved
0.6214	Remote Similarity	NPD6402	Approved
0.6207	Remote Similarity	NPD4756	Discovery
0.62	Remote Similarity	NPD5285	Approved
0.62	Remote Similarity	NPD5286	Approved
0.62	Remote Similarity	NPD4696	Approved
0.6196	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6014	Approved
0.619	Remote Similarity	NPD6012	Approved
0.619	Remote Similarity	NPD6013	Approved
0.6186	Remote Similarity	NPD6001	Approved
0.618	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD7331	Phase 2
0.6163	Remote Similarity	NPD8264	Approved
0.6162	Remote Similarity	NPD4755	Approved
0.6154	Remote Similarity	NPD5362	Discontinued
0.6154	Remote Similarity	NPD4788	Approved
0.6154	Remote Similarity	NPD5701	Approved
0.6146	Remote Similarity	NPD7637	Suspended
0.6146	Remote Similarity	NPD6411	Approved
0.6139	Remote Similarity	NPD5223	Approved
0.6132	Remote Similarity	NPD7102	Approved
0.6132	Remote Similarity	NPD7290	Approved
0.6132	Remote Similarity	NPD6883	Approved
0.6095	Remote Similarity	NPD7320	Approved
0.6078	Remote Similarity	NPD4633	Approved
0.6078	Remote Similarity	NPD5225	Approved
0.6078	Remote Similarity	NPD5224	Approved
0.6078	Remote Similarity	NPD5226	Approved
0.6075	Remote Similarity	NPD6650	Approved
0.6075	Remote Similarity	NPD6649	Approved
0.6075	Remote Similarity	NPD6869	Approved
0.6075	Remote Similarity	NPD6847	Approved
0.6075	Remote Similarity	NPD6617	Approved
0.6075	Remote Similarity	NPD8130	Phase 1
0.6044	Remote Similarity	NPD4269	Approved
0.6044	Remote Similarity	NPD4270	Approved
0.6044	Remote Similarity	NPD5209	Approved
0.6042	Remote Similarity	NPD4096	Approved
0.604	Remote Similarity	NPD4700	Approved
0.6038	Remote Similarity	NPD6372	Approved
0.6038	Remote Similarity	NPD6373	Approved
0.6019	Remote Similarity	NPD8297	Approved
0.6019	Remote Similarity	NPD5174	Approved
0.6019	Remote Similarity	NPD6882	Approved
0.6019	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD4252	Approved
0.5978	Remote Similarity	NPD7154	Phase 3
0.5963	Remote Similarity	NPD4632	Approved
0.596	Remote Similarity	NPD5654	Approved
0.596	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.596	Remote Similarity	NPD6049	Phase 2
0.5938	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6051	Approved
0.5938	Remote Similarity	NPD6101	Approved
0.5934	Remote Similarity	NPD4139	Approved
0.5934	Remote Similarity	NPD4692	Approved
0.5926	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD7632	Discontinued
0.5921	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5133	Approved
0.5909	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6008	Approved
0.5888	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD6698	Approved
0.5876	Remote Similarity	NPD46	Approved
0.5875	Remote Similarity	NPD368	Approved
0.5865	Remote Similarity	NPD4754	Approved
0.5856	Remote Similarity	NPD6274	Approved
0.5856	Remote Similarity	NPD6868	Approved
0.5854	Remote Similarity	NPD7341	Phase 2
0.5854	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6412	Phase 2
0.5842	Remote Similarity	NPD5959	Approved
0.5833	Remote Similarity	NPD4518	Approved
0.5833	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD4821	Approved
0.5824	Remote Similarity	NPD4819	Approved
0.5824	Remote Similarity	NPD4820	Approved
0.5824	Remote Similarity	NPD4822	Approved
0.5816	Remote Similarity	NPD8034	Phase 2

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