NPASS Compound

Structure

NPC180640 OpenBabel07101718242D 45 48 0 0 1 0 0 0 0 0999 V2000 -6.2335 -11.4080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2521 1.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5903 -0.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3222 0.5647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2186 -10.4081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3452 -9.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3302 -8.9213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4568 -8.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4418 -7.4344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5684 -6.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7917 -3.9736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7767 -2.9738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5535 -5.9475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6651 -4.4606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9033 -2.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4921 0.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7541 2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8584 -0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4412 3.1110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0938 4.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7169 1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3011 1.3254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 -0.0259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4488 1.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4452 3.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6801 -5.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8884 1.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 1.3254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8884 -1.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9921 2.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8584 0.5129 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9921 2.2764 0.0000 C 0 0 1 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 1.7468 0.9740 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1073 4.3007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4338 2.0516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8216 -5.9734 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7468 -0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5799 3.0854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2232 2.9158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3265 1.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5903 0.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 -0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 33 1 0 0 0 0 6 7 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 14 1 0 0 0 0 12 13 1 0 0 0 0 12 15 2 0 0 0 0 13 16 2 0 0 0 0 14 27 1 0 0 0 0 15 27 1 0 0 0 0 16 30 1 0 0 0 0 17 23 2 0 0 0 0 17 29 1 0 0 0 0 18 26 2 0 0 0 0 18 28 1 0 0 0 0 19 24 1 0 0 0 0 19 35 1 0 0 0 0 20 26 1 0 0 0 0 20 34 1 0 0 0 0 21 26 1 0 0 0 0 21 37 1 0 0 0 0 22 33 1 0 0 0 0 22 44 1 0 0 0 0 23 32 1 0 0 0 0 24 36 1 6 0 0 0 25 38 2 0 0 0 0 25 44 1 0 0 0 0 27 39 2 0 0 0 0 28 31 1 0 0 0 0 28 36 1 6 0 0 0 29 34 1 1 0 0 0 29 36 1 0 0 0 0 30 40 2 0 0 0 0 30 45 1 0 0 0 0 31 33 1 1 0 0 0 31 35 1 0 0 0 0 32 34 1 0 0 0 0 32 41 2 0 0 0 0 33 35 1 6 0 0 0 34 42 1 1 0 0 0 35 45 1 6 0 0 0 36 43 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	626.35
Volume:	655.006
LogP:	4.484
LogD:	3.359
LogS:	-4.6
# Rotatable Bonds:	16
TPSA:	147.43
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.083
Synthetic Accessibility Score:	5.353
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.911
MDCK Permeability:	2.980459430546034e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.303
Human Intestinal Absorption (HIA):	0.208
20% Bioavailability (F20%):	0.856
30% Bioavailability (F30%):	0.535

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.976
Plasma Protein Binding (PPB):	84.0301742553711%
Volume Distribution (VD):	0.691
Pgp-substrate:	11.79245376586914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.704
CYP2C19-substrate:	0.449
CYP2C9-inhibitor:	0.864
CYP2C9-substrate:	0.83
CYP2D6-inhibitor:	0.642
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.955
CYP3A4-substrate:	0.227

ADMET: Excretion

Clearance (CL):	1.616
Half-life (T1/2):	0.098

ADMET: Toxicity

hERG Blockers:	0.535
Human Hepatotoxicity (H-HT):	0.749
Drug-inuced Liver Injury (DILI):	0.322
AMES Toxicity:	0.159
Rat Oral Acute Toxicity:	0.934
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.914
Carcinogencity:	0.406
Eye Corrosion:	0.003
Eye Irritation:	0.038
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC180640

Natural Product ID:	NPC180640
*Common Name:**	Sapinsignoid C
IUPAC Name:	n.a.
Synonyms:	Sapinsignoid C
Standard InCHIKey:	GYANTJGKRSMADS-UVXJJLEESA-N
Standard InCHI:	InChI=1S/C36H50O9/c1-6-7-8-9-10-11-14-27(39)15-12-13-16-30(40)45-35-19-24(3)36(43)28(31(35)33(35,5)22-44-25(4)38)18-26(21-37)20-34(42)29(36)17-23(2)32(34)41/h12-13,15-18,24,28-29,31,37,42-43H,6-11,14,19-22H2,1-5H3/b15-12+,16-13+/t24-,28+,29-,31-,33-,34-,35+,36-/m1/s1
SMILES:	CCCCCCCCC(=O)/C=C/C=C/C(=O)O[C@@]12C[C@@H](C)[C@]3([C@@H](C=C(C[C@]4([C@H]3C=C(C)C4=O)O)CO)[C@@H]1[C@@]2(C)COC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2042142
PubChem CID:	57408528
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
NPO158	Sapium insigne	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22409148]
NPO158	Sapium insigne	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	400.0	nM	PMID[488216]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	2700.0	nM	PMID[488216]

☑ 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 NPC180640 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	233
0.1-0.2	1277
0.2-0.3	3963
0.3-0.4	6983
0.4-0.5	14352
0.5-0.6	9158
0.6-0.7	5427
0.7-0.8	1163
0.8-0.85	26
0.85-0.9	40
0.9-0.95	60
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9909	High Similarity	NPC19336
0.9909	High Similarity	NPC185876
0.9908	High Similarity	NPC472760
0.9817	High Similarity	NPC153651
0.9633	High Similarity	NPC474872
0.9561	High Similarity	NPC145238
0.9541	High Similarity	NPC474937
0.9541	High Similarity	NPC71889
0.945	High Similarity	NPC17138
0.945	High Similarity	NPC265499
0.945	High Similarity	NPC151216
0.945	High Similarity	NPC170212
0.945	High Similarity	NPC215643
0.945	High Similarity	NPC101825
0.945	High Similarity	NPC221511
0.945	High Similarity	NPC89227
0.945	High Similarity	NPC475391
0.9358	High Similarity	NPC96739
0.9358	High Similarity	NPC474871
0.9358	High Similarity	NPC475937
0.9358	High Similarity	NPC174471
0.9358	High Similarity	NPC158523
0.9358	High Similarity	NPC260786
0.9298	High Similarity	NPC52839
0.9266	High Similarity	NPC153036
0.9217	High Similarity	NPC257017
0.9217	High Similarity	NPC162009
0.9211	High Similarity	NPC157252
0.9211	High Similarity	NPC145182
0.9211	High Similarity	NPC472759
0.9211	High Similarity	NPC329080
0.9211	High Similarity	NPC471128
0.9211	High Similarity	NPC471126
0.9123	High Similarity	NPC5989
0.9123	High Similarity	NPC471108
0.9123	High Similarity	NPC236918
0.9123	High Similarity	NPC255081
0.9123	High Similarity	NPC5991
0.9123	High Similarity	NPC275696
0.9123	High Similarity	NPC156745
0.9123	High Similarity	NPC22628
0.9043	High Similarity	NPC475885
0.9035	High Similarity	NPC472397
0.9035	High Similarity	NPC472758
0.9035	High Similarity	NPC171905
0.9035	High Similarity	NPC471125
0.9018	High Similarity	NPC477091
0.8992	High Similarity	NPC236999
0.8974	High Similarity	NPC472399
0.8947	High Similarity	NPC10721
0.8889	High Similarity	NPC19464
0.887	High Similarity	NPC124676
0.887	High Similarity	NPC146280
0.886	High Similarity	NPC234858
0.886	High Similarity	NPC471127
0.886	High Similarity	NPC154363
0.8803	High Similarity	NPC472401
0.8783	High Similarity	NPC156252
0.875	High Similarity	NPC471940
0.8684	High Similarity	NPC472757
0.8667	High Similarity	NPC222307
0.8667	High Similarity	NPC471939
0.8609	High Similarity	NPC472400
0.8583	High Similarity	NPC473919
0.8583	High Similarity	NPC473709
0.8525	High Similarity	NPC270109
0.85	High Similarity	NPC473802
0.8333	Intermediate Similarity	NPC163004
0.8254	Intermediate Similarity	NPC469674
0.822	Intermediate Similarity	NPC148458
0.8205	Intermediate Similarity	NPC469463
0.8205	Intermediate Similarity	NPC469454
0.8205	Intermediate Similarity	NPC469496
0.8189	Intermediate Similarity	NPC100017
0.8189	Intermediate Similarity	NPC182266
0.8189	Intermediate Similarity	NPC471137
0.8189	Intermediate Similarity	NPC475500
0.8189	Intermediate Similarity	NPC223356
0.8189	Intermediate Similarity	NPC473548
0.8189	Intermediate Similarity	NPC471136
0.8189	Intermediate Similarity	NPC475154
0.8167	Intermediate Similarity	NPC472667
0.816	Intermediate Similarity	NPC221414
0.8142	Intermediate Similarity	NPC118911
0.8136	Intermediate Similarity	NPC133677
0.8136	Intermediate Similarity	NPC67290
0.8136	Intermediate Similarity	NPC138303
0.812	Intermediate Similarity	NPC123855
0.812	Intermediate Similarity	NPC76550
0.8067	Intermediate Similarity	NPC270958
0.8062	Intermediate Similarity	NPC68282
0.8051	Intermediate Similarity	NPC46269
0.8051	Intermediate Similarity	NPC106395
0.8051	Intermediate Similarity	NPC474271
0.8051	Intermediate Similarity	NPC25909
0.8034	Intermediate Similarity	NPC304180
0.8034	Intermediate Similarity	NPC179798
0.8031	Intermediate Similarity	NPC473485
0.8031	Intermediate Similarity	NPC475139
0.8031	Intermediate Similarity	NPC180902
0.8031	Intermediate Similarity	NPC474508
0.8017	Intermediate Similarity	NPC273433
0.8	Intermediate Similarity	NPC239273
0.7969	Intermediate Similarity	NPC469673
0.7966	Intermediate Similarity	NPC100267
0.7966	Intermediate Similarity	NPC71348
0.7966	Intermediate Similarity	NPC138757
0.7966	Intermediate Similarity	NPC475524
0.7965	Intermediate Similarity	NPC478156
0.7953	Intermediate Similarity	NPC251564
0.7953	Intermediate Similarity	NPC475314
0.7953	Intermediate Similarity	NPC475606
0.7953	Intermediate Similarity	NPC477189
0.7953	Intermediate Similarity	NPC196921
0.7953	Intermediate Similarity	NPC220757
0.7951	Intermediate Similarity	NPC145074
0.7951	Intermediate Similarity	NPC114939
0.7951	Intermediate Similarity	NPC143755
0.7951	Intermediate Similarity	NPC41123
0.7949	Intermediate Similarity	NPC5103
0.7949	Intermediate Similarity	NPC238850
0.7934	Intermediate Similarity	NPC257457
0.7934	Intermediate Similarity	NPC118638
0.7934	Intermediate Similarity	NPC311554
0.7931	Intermediate Similarity	NPC322903
0.7931	Intermediate Similarity	NPC102843
0.7931	Intermediate Similarity	NPC476479
0.7923	Intermediate Similarity	NPC243902
0.792	Intermediate Similarity	NPC63186
0.792	Intermediate Similarity	NPC15095
0.7907	Intermediate Similarity	NPC476823
0.7899	Intermediate Similarity	NPC56448
0.7899	Intermediate Similarity	NPC202889
0.7891	Intermediate Similarity	NPC34963
0.7886	Intermediate Similarity	NPC310511
0.7881	Intermediate Similarity	NPC475668
0.7881	Intermediate Similarity	NPC473921
0.7881	Intermediate Similarity	NPC475480
0.7874	Intermediate Similarity	NPC35109
0.7874	Intermediate Similarity	NPC162495
0.7869	Intermediate Similarity	NPC472933
0.7869	Intermediate Similarity	NPC470186
0.7863	Intermediate Similarity	NPC137911
0.7863	Intermediate Similarity	NPC228477
0.7851	Intermediate Similarity	NPC471854
0.7851	Intermediate Similarity	NPC474518
0.7851	Intermediate Similarity	NPC23046
0.7829	Intermediate Similarity	NPC58029
0.7829	Intermediate Similarity	NPC476111
0.7826	Intermediate Similarity	NPC239162
0.7823	Intermediate Similarity	NPC23786
0.7823	Intermediate Similarity	NPC470265
0.7823	Intermediate Similarity	NPC222688
0.782	Intermediate Similarity	NPC25887
0.7815	Intermediate Similarity	NPC317687
0.7815	Intermediate Similarity	NPC170487
0.7815	Intermediate Similarity	NPC221144
0.7812	Intermediate Similarity	NPC241935
0.7812	Intermediate Similarity	NPC279478
0.7807	Intermediate Similarity	NPC162973
0.7807	Intermediate Similarity	NPC155332
0.7807	Intermediate Similarity	NPC32577
0.7807	Intermediate Similarity	NPC475038
0.7807	Intermediate Similarity	NPC476081
0.7807	Intermediate Similarity	NPC114540
0.7807	Intermediate Similarity	NPC109195
0.7805	Intermediate Similarity	NPC48692
0.7805	Intermediate Similarity	NPC17938
0.7805	Intermediate Similarity	NPC476962
0.7797	Intermediate Similarity	NPC475134
0.7797	Intermediate Similarity	NPC477103
0.7797	Intermediate Similarity	NPC257240
0.7797	Intermediate Similarity	NPC475563
0.7795	Intermediate Similarity	NPC470850
0.7788	Intermediate Similarity	NPC470074
0.7788	Intermediate Similarity	NPC474718
0.7787	Intermediate Similarity	NPC21326
0.7787	Intermediate Similarity	NPC146786
0.7769	Intermediate Similarity	NPC176840
0.7769	Intermediate Similarity	NPC470793
0.7769	Intermediate Similarity	NPC179626
0.776	Intermediate Similarity	NPC469789
0.7759	Intermediate Similarity	NPC477125
0.7759	Intermediate Similarity	NPC34768
0.7759	Intermediate Similarity	NPC469607
0.7752	Intermediate Similarity	NPC471855
0.775	Intermediate Similarity	NPC159333
0.775	Intermediate Similarity	NPC472926
0.775	Intermediate Similarity	NPC471204
0.7742	Intermediate Similarity	NPC67569
0.7734	Intermediate Similarity	NPC104382
0.7734	Intermediate Similarity	NPC470851
0.7734	Intermediate Similarity	NPC471407
0.7731	Intermediate Similarity	NPC317107
0.7731	Intermediate Similarity	NPC231589
0.7731	Intermediate Similarity	NPC214797
0.7731	Intermediate Similarity	NPC287311
0.7731	Intermediate Similarity	NPC118860
0.773	Intermediate Similarity	NPC472398
0.7719	Intermediate Similarity	NPC115899

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 NPC180640 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	1540
0.2-0.3	3537
0.3-0.4	2424
0.4-0.5	973
0.5-0.6	295
0.6-0.7	166
0.7-0.8	9
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
0.7797	Intermediate Similarity	NPD6371	Approved
0.7583	Intermediate Similarity	NPD6650	Approved
0.7583	Intermediate Similarity	NPD6649	Approved
0.7521	Intermediate Similarity	NPD8297	Approved
0.7479	Intermediate Similarity	NPD6881	Approved
0.7479	Intermediate Similarity	NPD6899	Approved
0.7438	Intermediate Similarity	NPD8130	Phase 1
0.7419	Intermediate Similarity	NPD7115	Discovery
0.7417	Intermediate Similarity	NPD6373	Approved
0.7417	Intermediate Similarity	NPD6372	Approved
0.7395	Intermediate Similarity	NPD5697	Approved
0.7377	Intermediate Similarity	NPD6882	Approved
0.7355	Intermediate Similarity	NPD6883	Approved
0.7355	Intermediate Similarity	NPD7102	Approved
0.7355	Intermediate Similarity	NPD7290	Approved
0.7328	Intermediate Similarity	NPD7639	Approved
0.7328	Intermediate Similarity	NPD7640	Approved
0.7311	Intermediate Similarity	NPD6402	Approved
0.7311	Intermediate Similarity	NPD7128	Approved
0.7311	Intermediate Similarity	NPD5739	Approved
0.7311	Intermediate Similarity	NPD6675	Approved
0.7295	Intermediate Similarity	NPD6847	Approved
0.7295	Intermediate Similarity	NPD6869	Approved
0.7295	Intermediate Similarity	NPD6617	Approved
0.7273	Intermediate Similarity	NPD6012	Approved
0.7273	Intermediate Similarity	NPD6014	Approved
0.7273	Intermediate Similarity	NPD6013	Approved
0.725	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6319	Approved
0.7241	Intermediate Similarity	NPD7638	Approved
0.7209	Intermediate Similarity	NPD7604	Phase 2
0.7203	Intermediate Similarity	NPD5211	Phase 2
0.719	Intermediate Similarity	NPD7320	Approved
0.719	Intermediate Similarity	NPD6011	Approved
0.7179	Intermediate Similarity	NPD6648	Approved
0.7177	Intermediate Similarity	NPD4632	Approved
0.7119	Intermediate Similarity	NPD5344	Discontinued
0.7107	Intermediate Similarity	NPD5701	Approved
0.7091	Intermediate Similarity	NPD1696	Phase 3
0.7083	Intermediate Similarity	NPD5141	Approved
0.7073	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5286	Approved
0.7034	Intermediate Similarity	NPD4696	Approved
0.7034	Intermediate Similarity	NPD5285	Approved
0.7025	Intermediate Similarity	NPD6008	Approved
0.7023	Intermediate Similarity	NPD7492	Approved
0.7009	Intermediate Similarity	NPD6084	Phase 2
0.7009	Intermediate Similarity	NPD6083	Phase 2
0.7008	Intermediate Similarity	NPD6009	Approved
0.6992	Remote Similarity	NPD7736	Approved
0.6992	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6054	Approved
0.697	Remote Similarity	NPD7507	Approved
0.697	Remote Similarity	NPD6616	Approved
0.696	Remote Similarity	NPD6053	Discontinued
0.6949	Remote Similarity	NPD4225	Approved
0.693	Remote Similarity	NPD7838	Discovery
0.6923	Remote Similarity	NPD5983	Phase 2
0.6917	Remote Similarity	NPD5224	Approved
0.6917	Remote Similarity	NPD5225	Approved
0.6917	Remote Similarity	NPD7078	Approved
0.6917	Remote Similarity	NPD5226	Approved
0.6917	Remote Similarity	NPD4633	Approved
0.6911	Remote Similarity	NPD6686	Approved
0.6899	Remote Similarity	NPD7100	Approved
0.6899	Remote Similarity	NPD7101	Approved
0.688	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6370	Approved
0.6864	Remote Similarity	NPD4755	Approved
0.686	Remote Similarity	NPD5174	Approved
0.686	Remote Similarity	NPD5175	Approved
0.6842	Remote Similarity	NPD6336	Discontinued
0.6838	Remote Similarity	NPD7260	Phase 2
0.6838	Remote Similarity	NPD5695	Phase 3
0.6833	Remote Similarity	NPD5223	Approved
0.6829	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6335	Approved
0.6815	Remote Similarity	NPD7319	Approved
0.681	Remote Similarity	NPD5778	Approved
0.681	Remote Similarity	NPD5779	Approved
0.6807	Remote Similarity	NPD5696	Approved
0.6807	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4634	Approved
0.6797	Remote Similarity	NPD6274	Approved
0.6794	Remote Similarity	NPD8517	Approved
0.6794	Remote Similarity	NPD8515	Approved
0.6794	Remote Similarity	NPD6015	Approved
0.6794	Remote Similarity	NPD7503	Approved
0.6794	Remote Similarity	NPD8513	Phase 3
0.6794	Remote Similarity	NPD8516	Approved
0.6794	Remote Similarity	NPD6016	Approved
0.6791	Remote Similarity	NPD8293	Discontinued
0.6783	Remote Similarity	NPD46	Approved
0.6783	Remote Similarity	NPD6698	Approved
0.6783	Remote Similarity	NPD5785	Approved
0.6777	Remote Similarity	NPD7632	Discontinued
0.6774	Remote Similarity	NPD4730	Approved
0.6774	Remote Similarity	NPD4729	Approved
0.6752	Remote Similarity	NPD5282	Discontinued
0.675	Remote Similarity	NPD4700	Approved
0.6744	Remote Similarity	NPD6317	Approved
0.6742	Remote Similarity	NPD5988	Approved
0.6724	Remote Similarity	NPD7983	Approved
0.6724	Remote Similarity	NPD5284	Approved
0.6724	Remote Similarity	NPD5281	Approved
0.6723	Remote Similarity	NPD7902	Approved
0.6718	Remote Similarity	NPD6059	Approved
0.6696	Remote Similarity	NPD1695	Approved
0.6695	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5210	Approved
0.6695	Remote Similarity	NPD4629	Approved
0.6692	Remote Similarity	NPD7327	Approved
0.6692	Remote Similarity	NPD6313	Approved
0.6692	Remote Similarity	NPD7328	Approved
0.6692	Remote Similarity	NPD6314	Approved
0.6692	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6641	Remote Similarity	NPD7516	Approved
0.6639	Remote Similarity	NPD5222	Approved
0.6639	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5221	Approved
0.6637	Remote Similarity	NPD1694	Approved
0.6614	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD4767	Approved
0.6613	Remote Similarity	NPD4768	Approved
0.661	Remote Similarity	NPD7748	Approved
0.6591	Remote Similarity	NPD8377	Approved
0.6591	Remote Similarity	NPD8294	Approved
0.6583	Remote Similarity	NPD5173	Approved
0.6581	Remote Similarity	NPD5694	Approved
0.6581	Remote Similarity	NPD6079	Approved
0.6581	Remote Similarity	NPD6050	Approved
0.6581	Remote Similarity	NPD7637	Suspended
0.6581	Remote Similarity	NPD5693	Phase 1
0.6552	Remote Similarity	NPD4753	Phase 2
0.6544	Remote Similarity	NPD8074	Phase 3
0.6541	Remote Similarity	NPD8296	Approved
0.6541	Remote Similarity	NPD6908	Approved
0.6541	Remote Similarity	NPD8378	Approved
0.6541	Remote Similarity	NPD6909	Approved
0.6541	Remote Similarity	NPD8380	Approved
0.6541	Remote Similarity	NPD8335	Approved
0.6541	Remote Similarity	NPD8379	Approved
0.6541	Remote Similarity	NPD6921	Approved
0.6538	Remote Similarity	NPD6868	Approved
0.6518	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD8133	Approved
0.6508	Remote Similarity	NPD5128	Approved
0.65	Remote Similarity	NPD4697	Phase 3
0.6496	Remote Similarity	NPD5692	Phase 3
0.6484	Remote Similarity	NPD5216	Approved
0.6484	Remote Similarity	NPD5217	Approved
0.6484	Remote Similarity	NPD5215	Approved
0.6471	Remote Similarity	NPD7900	Approved
0.6471	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6672	Approved
0.6466	Remote Similarity	NPD5737	Approved
0.6452	Remote Similarity	NPD4754	Approved
0.6443	Remote Similarity	NPD7236	Approved
0.6441	Remote Similarity	NPD6411	Approved
0.6441	Remote Similarity	NPD7515	Phase 2
0.6429	Remote Similarity	NPD6845	Suspended
0.641	Remote Similarity	NPD6080	Approved
0.641	Remote Similarity	NPD5328	Approved
0.641	Remote Similarity	NPD6673	Approved
0.641	Remote Similarity	NPD6904	Approved
0.6406	Remote Similarity	NPD5169	Approved
0.6406	Remote Similarity	NPD5135	Approved
0.6406	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4202	Approved
0.6379	Remote Similarity	NPD3573	Approved
0.6372	Remote Similarity	NPD5209	Approved
0.6364	Remote Similarity	NPD7839	Suspended
0.6364	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD5127	Approved
0.6356	Remote Similarity	NPD5207	Approved
0.6348	Remote Similarity	NPD5363	Approved
0.634	Remote Similarity	NPD7239	Suspended
0.6333	Remote Similarity	NPD6001	Approved
0.6328	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7154	Phase 3
0.6316	Remote Similarity	NPD5362	Discontinued
0.6311	Remote Similarity	NPD5959	Approved
0.6303	Remote Similarity	NPD8034	Phase 2
0.6303	Remote Similarity	NPD8035	Phase 2
0.6299	Remote Similarity	NPD6412	Phase 2
0.6293	Remote Similarity	NPD5690	Phase 2
0.6293	Remote Similarity	NPD5279	Phase 3
0.6293	Remote Similarity	NPD3618	Phase 1
0.6293	Remote Similarity	NPD5280	Approved
0.6293	Remote Similarity	NPD4694	Approved

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