NPASS Compound

Structure

CID47951 OpenBabel06191715382D 35 38 0 0 1 0 0 0 0 0999 V2000 -1.8191 -5.9406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1411 -2.1382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2212 1.7346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5134 2.1607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3597 0.5695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2508 -0.3972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6350 -5.4108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5840 -4.4394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3999 -3.9095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3490 -2.9381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1648 -2.4083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1139 -1.4369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2471 -0.9953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1962 -0.0238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2395 -1.2395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9976 1.4460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1838 1.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5134 -1.2395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5333 1.0467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0309 1.3371 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7529 -0.7261 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6854 0.7581 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3295 0.4178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5765 -0.2085 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.7261 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8347 -0.4048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6469 0.3296 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4681 0.1805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5134 0.5134 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 -2.2786 1.3892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8987 -1.0983 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5410 -1.7805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7317 -0.6410 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5137 -0.1120 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 14 23 1 0 0 0 0 15 18 2 0 0 0 0 16 20 1 0 0 0 0 17 19 2 0 0 0 0 17 29 1 0 0 0 0 18 25 1 0 0 0 0 19 27 1 0 0 0 0 20 29 1 6 0 0 0 21 15 1 6 0 0 0 21 24 1 0 0 0 0 21 26 1 0 0 0 0 22 16 1 1 0 0 0 22 24 1 0 0 0 0 22 28 1 0 0 0 0 23 31 2 0 0 0 0 23 35 1 0 0 0 0 24 28 1 1 0 0 0 25 30 1 1 0 0 0 25 32 1 0 0 0 0 26 29 1 0 0 0 0 26 33 2 0 0 0 0 27 30 1 1 0 0 0 27 35 1 0 0 0 0 29 30 1 1 0 0 0 30 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.3
Volume:	521.343
LogP:	5.981
LogD:	4.757
LogS:	-5.33
# Rotatable Bonds:	8
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.229
Synthetic Accessibility Score:	6.471
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.723
MDCK Permeability:	2.4197737729991786e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.623
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.917
30% Bioavailability (F30%):	0.807

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	96.86333465576172%
Volume Distribution (VD):	1.191
Pgp-substrate:	2.0380353927612305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.069
CYP1A2-substrate:	0.109
CYP2C19-inhibitor:	0.265
CYP2C19-substrate:	0.618
CYP2C9-inhibitor:	0.776
CYP2C9-substrate:	0.11
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.871
CYP3A4-substrate:	0.487

ADMET: Excretion

Clearance (CL):	7.999
Half-life (T1/2):	0.043

ADMET: Toxicity

hERG Blockers:	0.595
Human Hepatotoxicity (H-HT):	0.493
Drug-inuced Liver Injury (DILI):	0.129
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.799
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.955
Carcinogencity:	0.353
Eye Corrosion:	0.005
Eye Irritation:	0.012
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC47951

Natural Product ID:	NPC47951
*Common Name:**	JZIBSDBSLIKLEM-SPXYNGGESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JZIBSDBSLIKLEM-SPXYNGGESA-N
Standard InCHI:	InChI=1S/C30H42O5/c1-7-8-9-10-11-12-13-14-23(31)35-27-19(3)17-29-20(4)16-22-24(28(22,5)6)21(26(29)33)15-18(2)25(32)30(27,29)34/h11-15,17,20-22,24-25,27,32,34H,7-10,16H2,1-6H3/b12-11-,14-13+/t20-,21+,22-,24+,25-,27+,29+,30+/m1/s1
SMILES:	CCCCC/C=CC=CC(=O)O[C@H]1C(=C[C@]23[C@]1(O)[C@H](O)C(=C[C@H](C3=O)[C@H]1[C@@H](C[C@H]2C)C1(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3815033
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane 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
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[12350140]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[12762796]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387657]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[1955882]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	14100.0	nM	PMID[558920]

☑ 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 NPC47951 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	237
0.1-0.2	1281
0.2-0.3	4608
0.3-0.4	9419
0.4-0.5	15227
0.5-0.6	7664
0.6-0.7	3557
0.7-0.8	661
0.8-0.85	9
0.85-0.9	10
0.9-0.95	7
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9709	High Similarity	NPC138757
0.9615	High Similarity	NPC106395
0.9615	High Similarity	NPC46269
0.9524	High Similarity	NPC67290
0.9524	High Similarity	NPC138303
0.9524	High Similarity	NPC133677
0.9519	High Similarity	NPC76550
0.9519	High Similarity	NPC123855
0.9327	High Similarity	NPC257240
0.9048	High Similarity	NPC477102
0.8962	High Similarity	NPC477103
0.8952	High Similarity	NPC308191
0.8942	High Similarity	NPC179891
0.8762	High Similarity	NPC475661
0.8762	High Similarity	NPC473488
0.8704	High Similarity	NPC287311
0.8679	High Similarity	NPC473911
0.8333	Intermediate Similarity	NPC167219
0.8318	Intermediate Similarity	NPC309190
0.8252	Intermediate Similarity	NPC261341
0.819	Intermediate Similarity	NPC141191
0.8155	Intermediate Similarity	NPC65829
0.8148	Intermediate Similarity	NPC203659
0.8103	Intermediate Similarity	NPC475885
0.8095	Intermediate Similarity	NPC169205
0.8056	Intermediate Similarity	NPC110989
0.8037	Intermediate Similarity	NPC206079
0.8036	Intermediate Similarity	NPC470961
0.8017	Intermediate Similarity	NPC156745
0.8017	Intermediate Similarity	NPC236918
0.8	Intermediate Similarity	NPC185553
0.7982	Intermediate Similarity	NPC100487
0.7965	Intermediate Similarity	NPC191620
0.7963	Intermediate Similarity	NPC225353
0.7949	Intermediate Similarity	NPC329080
0.7949	Intermediate Similarity	NPC472759
0.7946	Intermediate Similarity	NPC29133
0.7934	Intermediate Similarity	NPC236999
0.7909	Intermediate Similarity	NPC243998
0.7905	Intermediate Similarity	NPC193645
0.7905	Intermediate Similarity	NPC48803
0.7905	Intermediate Similarity	NPC275960
0.7905	Intermediate Similarity	NPC90121
0.79	Intermediate Similarity	NPC11804
0.789	Intermediate Similarity	NPC475945
0.789	Intermediate Similarity	NPC475871
0.7885	Intermediate Similarity	NPC469645
0.7885	Intermediate Similarity	NPC469692
0.7881	Intermediate Similarity	NPC470829
0.7881	Intermediate Similarity	NPC473228
0.787	Intermediate Similarity	NPC474742
0.787	Intermediate Similarity	NPC477950
0.7864	Intermediate Similarity	NPC145666
0.7863	Intermediate Similarity	NPC264954
0.7863	Intermediate Similarity	NPC477092
0.785	Intermediate Similarity	NPC64742
0.7845	Intermediate Similarity	NPC183580
0.7845	Intermediate Similarity	NPC471145
0.7845	Intermediate Similarity	NPC312824
0.7845	Intermediate Similarity	NPC470493
0.7838	Intermediate Similarity	NPC26617
0.7833	Intermediate Similarity	NPC145238
0.783	Intermediate Similarity	NPC9812
0.7818	Intermediate Similarity	NPC474741
0.7812	Intermediate Similarity	NPC52523
0.7812	Intermediate Similarity	NPC217673
0.781	Intermediate Similarity	NPC53685
0.781	Intermediate Similarity	NPC121825
0.7798	Intermediate Similarity	NPC118405
0.7798	Intermediate Similarity	NPC86077
0.7798	Intermediate Similarity	NPC474747
0.7797	Intermediate Similarity	NPC19336
0.7797	Intermediate Similarity	NPC185876
0.7797	Intermediate Similarity	NPC474370
0.7788	Intermediate Similarity	NPC261607
0.7788	Intermediate Similarity	NPC300312
0.7788	Intermediate Similarity	NPC111114
0.7778	Intermediate Similarity	NPC124676
0.7778	Intermediate Similarity	NPC146280
0.7778	Intermediate Similarity	NPC469872
0.7778	Intermediate Similarity	NPC472760
0.7778	Intermediate Similarity	NPC186525
0.7778	Intermediate Similarity	NPC469864
0.7778	Intermediate Similarity	NPC475401
0.7768	Intermediate Similarity	NPC220155
0.7767	Intermediate Similarity	NPC170775
0.7759	Intermediate Similarity	NPC471127
0.7759	Intermediate Similarity	NPC234858
0.7759	Intermediate Similarity	NPC154363
0.7757	Intermediate Similarity	NPC477949
0.775	Intermediate Similarity	NPC472399
0.7748	Intermediate Similarity	NPC223450
0.7736	Intermediate Similarity	NPC304886
0.7727	Intermediate Similarity	NPC183570
0.7727	Intermediate Similarity	NPC472755
0.7719	Intermediate Similarity	NPC71680
0.7712	Intermediate Similarity	NPC180640
0.7706	Intermediate Similarity	NPC150923
0.7706	Intermediate Similarity	NPC116139
0.7706	Intermediate Similarity	NPC472753
0.7705	Intermediate Similarity	NPC471940
0.77	Intermediate Similarity	NPC161045
0.7699	Intermediate Similarity	NPC475065
0.7692	Intermediate Similarity	NPC167606
0.7692	Intermediate Similarity	NPC140055
0.7692	Intermediate Similarity	NPC473448
0.7692	Intermediate Similarity	NPC469368
0.7692	Intermediate Similarity	NPC286528
0.7692	Intermediate Similarity	NPC20302
0.7692	Intermediate Similarity	NPC475305
0.7692	Intermediate Similarity	NPC10721
0.7692	Intermediate Similarity	NPC470492
0.7685	Intermediate Similarity	NPC244411
0.7679	Intermediate Similarity	NPC329048
0.7679	Intermediate Similarity	NPC330011
0.7672	Intermediate Similarity	NPC472400
0.7667	Intermediate Similarity	NPC88326
0.7667	Intermediate Similarity	NPC162009
0.7667	Intermediate Similarity	NPC153700
0.7667	Intermediate Similarity	NPC257017
0.7658	Intermediate Similarity	NPC472756
0.7647	Intermediate Similarity	NPC145182
0.7647	Intermediate Similarity	NPC471128
0.7647	Intermediate Similarity	NPC157252
0.7647	Intermediate Similarity	NPC471126
0.7636	Intermediate Similarity	NPC472754
0.7636	Intermediate Similarity	NPC66110
0.7632	Intermediate Similarity	NPC15551
0.7632	Intermediate Similarity	NPC181298
0.7627	Intermediate Similarity	NPC13710
0.7627	Intermediate Similarity	NPC709
0.7627	Intermediate Similarity	NPC50774
0.7623	Intermediate Similarity	NPC471939
0.7619	Intermediate Similarity	NPC476705
0.7619	Intermediate Similarity	NPC150978
0.7619	Intermediate Similarity	NPC74103
0.7619	Intermediate Similarity	NPC70595
0.7619	Intermediate Similarity	NPC284185
0.7619	Intermediate Similarity	NPC123177
0.7615	Intermediate Similarity	NPC475053
0.7615	Intermediate Similarity	NPC290802
0.7611	Intermediate Similarity	NPC318363
0.7611	Intermediate Similarity	NPC475418
0.7611	Intermediate Similarity	NPC473482
0.7607	Intermediate Similarity	NPC64318
0.7593	Intermediate Similarity	NPC213947
0.7593	Intermediate Similarity	NPC170143
0.7593	Intermediate Similarity	NPC108475
0.7586	Intermediate Similarity	NPC71889
0.7586	Intermediate Similarity	NPC472757
0.7583	Intermediate Similarity	NPC52839
0.7583	Intermediate Similarity	NPC472401
0.7573	Intermediate Similarity	NPC72513
0.757	Intermediate Similarity	NPC209355
0.757	Intermediate Similarity	NPC469873
0.7568	Intermediate Similarity	NPC475873
0.7568	Intermediate Similarity	NPC280566
0.7565	Intermediate Similarity	NPC474315
0.7549	Intermediate Similarity	NPC21471
0.7549	Intermediate Similarity	NPC261380
0.7549	Intermediate Similarity	NPC33570
0.7549	Intermediate Similarity	NPC165162
0.7545	Intermediate Similarity	NPC244456
0.7545	Intermediate Similarity	NPC171759
0.7545	Intermediate Similarity	NPC469657
0.7545	Intermediate Similarity	NPC62670
0.7545	Intermediate Similarity	NPC185141
0.7545	Intermediate Similarity	NPC128733
0.7545	Intermediate Similarity	NPC110443
0.7545	Intermediate Similarity	NPC133907
0.7545	Intermediate Similarity	NPC46998
0.7544	Intermediate Similarity	NPC228477
0.7544	Intermediate Similarity	NPC137911
0.7544	Intermediate Similarity	NPC475274
0.7542	Intermediate Similarity	NPC153651
0.7542	Intermediate Similarity	NPC156252
0.7542	Intermediate Similarity	NPC475323
0.7542	Intermediate Similarity	NPC471146
0.7541	Intermediate Similarity	NPC473709
0.7541	Intermediate Similarity	NPC473919
0.7541	Intermediate Similarity	NPC8374
0.7524	Intermediate Similarity	NPC77337
0.7524	Intermediate Similarity	NPC129419
0.7524	Intermediate Similarity	NPC253144
0.7523	Intermediate Similarity	NPC161855
0.7522	Intermediate Similarity	NPC473284
0.7522	Intermediate Similarity	NPC91034
0.7521	Intermediate Similarity	NPC305044
0.7521	Intermediate Similarity	NPC265290
0.7521	Intermediate Similarity	NPC19464
0.7521	Intermediate Similarity	NPC474872
0.7521	Intermediate Similarity	NPC147912
0.7521	Intermediate Similarity	NPC67259
0.75	Intermediate Similarity	NPC241477
0.75	Intermediate Similarity	NPC220964
0.75	Intermediate Similarity	NPC475970
0.75	Intermediate Similarity	NPC476803
0.75	Intermediate Similarity	NPC272632
0.75	Intermediate Similarity	NPC121099
0.75	Intermediate Similarity	NPC475676

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 NPC47951 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	1739
0.2-0.3	3621
0.3-0.4	2368
0.4-0.5	875
0.5-0.6	275
0.6-0.7	42
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9327	High Similarity	NPD6371	Approved
0.8039	Intermediate Similarity	NPD5785	Approved
0.7905	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7115	Discovery
0.76	Intermediate Similarity	NPD5209	Approved
0.7549	Intermediate Similarity	NPD5363	Approved
0.7364	Intermediate Similarity	NPD4225	Approved
0.7255	Intermediate Similarity	NPD4269	Approved
0.7255	Intermediate Similarity	NPD4270	Approved
0.7196	Intermediate Similarity	NPD7838	Discovery
0.7184	Intermediate Similarity	NPD5362	Discontinued
0.7157	Intermediate Similarity	NPD5369	Approved
0.7143	Intermediate Similarity	NPD5786	Approved
0.713	Intermediate Similarity	NPD7983	Approved
0.7059	Intermediate Similarity	NPD4252	Approved
0.7037	Intermediate Similarity	NPD6698	Approved
0.7037	Intermediate Similarity	NPD46	Approved
0.7019	Intermediate Similarity	NPD7154	Phase 3
0.6944	Remote Similarity	NPD1695	Approved
0.6909	Remote Similarity	NPD5779	Approved
0.6909	Remote Similarity	NPD5778	Approved
0.6863	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7637	Suspended
0.6818	Remote Similarity	NPD6411	Approved
0.6754	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4822	Approved
0.6731	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4821	Approved
0.6731	Remote Similarity	NPD4819	Approved
0.6731	Remote Similarity	NPD4820	Approved
0.6723	Remote Similarity	NPD6686	Approved
0.6696	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6639	Remote Similarity	NPD8297	Approved
0.6638	Remote Similarity	NPD5344	Discontinued
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6101	Approved
0.6604	Remote Similarity	NPD6435	Approved
0.6583	Remote Similarity	NPD6881	Approved
0.6583	Remote Similarity	NPD6899	Approved
0.6574	Remote Similarity	NPD1694	Approved
0.6574	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6649	Approved
0.6557	Remote Similarity	NPD6650	Approved
0.6552	Remote Similarity	NPD6648	Approved
0.6542	Remote Similarity	NPD5331	Approved
0.6542	Remote Similarity	NPD5332	Approved
0.6538	Remote Similarity	NPD4271	Approved
0.6538	Remote Similarity	NPD4268	Approved
0.6535	Remote Similarity	NPD6319	Approved
0.6518	Remote Similarity	NPD5281	Approved
0.6518	Remote Similarity	NPD5284	Approved
0.6509	Remote Similarity	NPD4790	Discontinued
0.6504	Remote Similarity	NPD6053	Discontinued
0.65	Remote Similarity	NPD5697	Approved
0.6491	Remote Similarity	NPD5695	Phase 3
0.6484	Remote Similarity	NPD8513	Phase 3
0.6484	Remote Similarity	NPD8517	Approved
0.6484	Remote Similarity	NPD8515	Approved
0.6484	Remote Similarity	NPD8516	Approved
0.6475	Remote Similarity	NPD7290	Approved
0.6475	Remote Similarity	NPD7102	Approved
0.6475	Remote Similarity	NPD6883	Approved
0.6466	Remote Similarity	NPD5696	Approved
0.6449	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD7839	Suspended
0.6423	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6617	Approved
0.6423	Remote Similarity	NPD8130	Phase 1
0.6423	Remote Similarity	NPD6869	Approved
0.6423	Remote Similarity	NPD6847	Approved
0.6422	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD5739	Approved
0.6417	Remote Similarity	NPD6675	Approved
0.6417	Remote Similarity	NPD6402	Approved
0.6417	Remote Similarity	NPD7128	Approved
0.6415	Remote Similarity	NPD5368	Approved
0.6412	Remote Similarity	NPD8273	Phase 1
0.641	Remote Similarity	NPD7640	Approved
0.641	Remote Similarity	NPD7639	Approved
0.6393	Remote Similarity	NPD6373	Approved
0.6393	Remote Similarity	NPD6012	Approved
0.6393	Remote Similarity	NPD6372	Approved
0.6393	Remote Similarity	NPD6013	Approved
0.6393	Remote Similarity	NPD6014	Approved
0.6391	Remote Similarity	NPD7319	Approved
0.6371	Remote Similarity	NPD6882	Approved
0.6357	Remote Similarity	NPD7503	Approved
0.6348	Remote Similarity	NPD4629	Approved
0.6348	Remote Similarity	NPD5210	Approved
0.6348	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5370	Suspended
0.6336	Remote Similarity	NPD7492	Approved
0.6325	Remote Similarity	NPD7638	Approved
0.632	Remote Similarity	NPD4632	Approved
0.6316	Remote Similarity	NPD6399	Phase 3
0.6311	Remote Similarity	NPD7320	Approved
0.6311	Remote Similarity	NPD6011	Approved
0.6306	Remote Similarity	NPD7524	Approved
0.6306	Remote Similarity	NPD4251	Approved
0.6306	Remote Similarity	NPD4250	Approved
0.6303	Remote Similarity	NPD5211	Phase 2
0.6296	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD7507	Approved
0.6288	Remote Similarity	NPD6616	Approved
0.6283	Remote Similarity	NPD5207	Approved
0.6279	Remote Similarity	NPD6054	Approved
0.6273	Remote Similarity	NPD1696	Phase 3
0.626	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7604	Phase 2
0.625	Remote Similarity	NPD8039	Approved
0.6241	Remote Similarity	NPD8074	Phase 3
0.6241	Remote Similarity	NPD7078	Approved
0.623	Remote Similarity	NPD6412	Phase 2
0.623	Remote Similarity	NPD5701	Approved
0.6228	Remote Similarity	NPD5694	Approved
0.6228	Remote Similarity	NPD5693	Phase 1
0.6228	Remote Similarity	NPD6050	Approved
0.6228	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD7334	Approved
0.6216	Remote Similarity	NPD5330	Approved
0.6216	Remote Similarity	NPD6409	Approved
0.6216	Remote Similarity	NPD7146	Approved
0.6216	Remote Similarity	NPD6684	Approved
0.6216	Remote Similarity	NPD7521	Approved
0.6216	Remote Similarity	NPD4249	Approved
0.621	Remote Similarity	NPD4634	Approved
0.6198	Remote Similarity	NPD5141	Approved
0.6195	Remote Similarity	NPD4753	Phase 2
0.6194	Remote Similarity	NPD7736	Approved
0.6183	Remote Similarity	NPD6370	Approved
0.6182	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.616	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5692	Phase 3
0.6136	Remote Similarity	NPD7829	Approved
0.6136	Remote Similarity	NPD7830	Approved
0.6136	Remote Similarity	NPD7642	Approved
0.6134	Remote Similarity	NPD5285	Approved
0.6134	Remote Similarity	NPD4696	Approved
0.6134	Remote Similarity	NPD5286	Approved
0.6116	Remote Similarity	NPD6647	Phase 2
0.6107	Remote Similarity	NPD6016	Approved
0.6107	Remote Similarity	NPD6015	Approved
0.6106	Remote Similarity	NPD4518	Approved
0.6106	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6903	Approved
0.6091	Remote Similarity	NPD6695	Phase 3
0.608	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD7101	Approved
0.6077	Remote Similarity	NPD7100	Approved
0.6071	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5279	Phase 3
0.6061	Remote Similarity	NPD5988	Approved
0.6058	Remote Similarity	NPD7260	Phase 2
0.6053	Remote Similarity	NPD6673	Approved
0.6053	Remote Similarity	NPD6080	Approved
0.6053	Remote Similarity	NPD6904	Approved
0.6047	Remote Similarity	NPD6009	Approved
0.6036	Remote Similarity	NPD3133	Approved
0.6036	Remote Similarity	NPD3665	Phase 1
0.6036	Remote Similarity	NPD3666	Approved
0.6036	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD5224	Approved
0.6033	Remote Similarity	NPD5226	Approved
0.6033	Remote Similarity	NPD4633	Approved
0.6033	Remote Similarity	NPD5225	Approved
0.6032	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD6059	Approved
0.6017	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD8293	Discontinued
0.6	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD7328	Approved
0.6	Remote Similarity	NPD6335	Approved
0.5985	Remote Similarity	NPD5983	Phase 2
0.5985	Remote Similarity	NPD8033	Approved
0.5984	Remote Similarity	NPD5174	Approved
0.5984	Remote Similarity	NPD5175	Approved
0.5983	Remote Similarity	NPD7748	Approved
0.5983	Remote Similarity	NPD6001	Approved
0.5981	Remote Similarity	NPD4756	Discovery
0.5969	Remote Similarity	NPD6274	Approved
0.5966	Remote Similarity	NPD7902	Approved
0.5966	Remote Similarity	NPD5959	Approved
0.5966	Remote Similarity	NPD4755	Approved
0.5965	Remote Similarity	NPD5737	Approved
0.5965	Remote Similarity	NPD6672	Approved
0.5963	Remote Similarity	NPD7332	Phase 2
0.5954	Remote Similarity	NPD7516	Approved
0.595	Remote Similarity	NPD5223	Approved
0.5948	Remote Similarity	NPD7515	Phase 2
0.5948	Remote Similarity	NPD6079	Approved
0.5929	Remote Similarity	NPD5280	Approved
0.5929	Remote Similarity	NPD4623	Approved
0.5929	Remote Similarity	NPD4694	Approved
0.5929	Remote Similarity	NPD5690	Phase 2
0.5929	Remote Similarity	NPD3574	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