NPASS Compound

Structure

CID18211 OpenBabel06191715342D 30 33 0 0 1 0 0 0 0 0999 V2000 -1.4417 -6.6129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9417 -5.7469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6129 -2.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1488 0.5583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7469 0.0583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7346 -2.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9417 -4.0148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4417 -0.7346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9417 -4.0148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0148 -2.9417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1564 -0.9877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4417 -3.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7346 -1.4417 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4417 -3.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4417 -0.7346 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1488 -2.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1488 -1.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4417 -4.8808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4417 -4.8808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8808 -2.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0148 -0.9417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8808 -1.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9877 0.1564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4417 1.0474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9417 -5.7469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9417 -5.7469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7469 -2.9417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0148 0.0583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7469 -0.9417 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 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 12 1 0 0 0 0 7 12 2 0 0 0 0 7 18 1 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 16 2 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 30 1 0 0 0 0 12 14 1 0 0 0 0 13 6 1 6 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 8 1 1 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 17 21 2 0 0 0 0 18 19 2 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 22 2 0 0 0 0 20 27 1 0 0 0 0 21 22 1 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 23 24 2 0 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.17
Volume:	415.215
LogP:	3.245
LogD:	3.092
LogS:	-4.718
# Rotatable Bonds:	5
TPSA:	72.45
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.695
Synthetic Accessibility Score:	3.416
Fsp3:	0.435
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.709
MDCK Permeability:	3.729417221620679e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.123

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.134
Plasma Protein Binding (PPB):	79.8868179321289%
Volume Distribution (VD):	0.663
Pgp-substrate:	14.17848014831543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.1
CYP1A2-substrate:	0.972
CYP2C19-inhibitor:	0.573
CYP2C19-substrate:	0.911
CYP2C9-inhibitor:	0.283
CYP2C9-substrate:	0.864
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.798
CYP3A4-substrate:	0.86

ADMET: Excretion

Clearance (CL):	8.522
Half-life (T1/2):	0.362

ADMET: Toxicity

hERG Blockers:	0.21
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.872
AMES Toxicity:	0.09
Rat Oral Acute Toxicity:	0.242
Maximum Recommended Daily Dose:	0.541
Skin Sensitization:	0.679
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.474

Download Data

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

Natural Product: NPC18211

Natural Product ID:	NPC18211
*Common Name:**	Neoisostegane
IUPAC Name:	n.a.
Synonyms:	Neoisostegane
Standard InCHIKey:	UAFHDDGMOVOBAW-DZGCQCFKSA-N
Standard InCHI:	InChI=1S/C23H26O7/c1-25-18-7-12-6-13-11-30-23(24)15(13)8-17-16(14(12)9-19(18)26-2)10-20(27-3)22(29-5)21(17)28-4/h7,9-10,13,15H,6,8,11H2,1-5H3/t13-,15+/m0/s1
SMILES:	COc1cc2C[C@H]3COC(=O)[C@@H]3Cc3c(-c2cc1OC)cc(c(c3OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483208
PubChem CID:	442918
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001510] Lignan 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
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11720541]
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6208342]
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[8133298]
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16145	Apocynum venetum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10276	Physochlaina physaloides	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16145	Apocynum venetum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16145	Apocynum venetum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16145	Apocynum venetum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10276	Physochlaina physaloides	Species	Solanaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	6.6	ug ml-1	PMID[513280]

☑ 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 NPC18211 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	367
0.1-0.2	1490
0.2-0.3	3340
0.3-0.4	8235
0.4-0.5	10697
0.5-0.6	3626
0.6-0.7	8123
0.7-0.8	6322
0.8-0.85	382
0.85-0.9	101
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9854	High Similarity	NPC143092
0.927	High Similarity	NPC72796
0.927	High Similarity	NPC44245
0.927	High Similarity	NPC211386
0.9241	High Similarity	NPC303519
0.9116	High Similarity	NPC474514
0.9067	High Similarity	NPC325122
0.906	High Similarity	NPC477380
0.9054	High Similarity	NPC178195
0.9054	High Similarity	NPC348849
0.9028	High Similarity	NPC321958
0.9028	High Similarity	NPC321696
0.9	High Similarity	NPC865
0.9	High Similarity	NPC477885
0.8958	High Similarity	NPC318286
0.8958	High Similarity	NPC327651
0.8951	High Similarity	NPC218510
0.8951	High Similarity	NPC76415
0.8929	High Similarity	NPC471182
0.8926	High Similarity	NPC273578
0.8919	High Similarity	NPC220577
0.8912	High Similarity	NPC149505
0.8889	High Similarity	NPC474036
0.8889	High Similarity	NPC61141
0.8889	High Similarity	NPC326144
0.8881	High Similarity	NPC40237
0.8881	High Similarity	NPC210354
0.8881	High Similarity	NPC176586
0.8881	High Similarity	NPC151423
0.8836	High Similarity	NPC104024
0.8836	High Similarity	NPC101755
0.8836	High Similarity	NPC65574
0.8836	High Similarity	NPC80230
0.8836	High Similarity	NPC304687
0.8819	High Similarity	NPC470811
0.8819	High Similarity	NPC106920
0.8819	High Similarity	NPC477697
0.8819	High Similarity	NPC477696
0.8819	High Similarity	NPC273657
0.8784	High Similarity	NPC316989
0.8776	High Similarity	NPC198129
0.8776	High Similarity	NPC252281
0.8776	High Similarity	NPC477375
0.8776	High Similarity	NPC327352
0.8767	High Similarity	NPC87295
0.8759	High Similarity	NPC177644
0.8759	High Similarity	NPC218841
0.8759	High Similarity	NPC475000
0.8759	High Similarity	NPC92693
0.8759	High Similarity	NPC191158
0.8742	High Similarity	NPC238834
0.8725	High Similarity	NPC210642
0.8725	High Similarity	NPC13985
0.8716	High Similarity	NPC477376
0.8716	High Similarity	NPC477374
0.8716	High Similarity	NPC262455
0.8716	High Similarity	NPC322426
0.8716	High Similarity	NPC85141
0.8716	High Similarity	NPC177476
0.8705	High Similarity	NPC141493
0.8705	High Similarity	NPC184928
0.8699	High Similarity	NPC27106
0.8686	High Similarity	NPC223807
0.8667	High Similarity	NPC104353
0.8667	High Similarity	NPC473732
0.8662	High Similarity	NPC209229
0.8654	High Similarity	NPC477884
0.8652	High Similarity	NPC185680
0.8652	High Similarity	NPC256776
0.8652	High Similarity	NPC145722
0.8649	High Similarity	NPC40654
0.8649	High Similarity	NPC262804
0.8649	High Similarity	NPC325720
0.8649	High Similarity	NPC304821
0.8649	High Similarity	NPC316676
0.8649	High Similarity	NPC477879
0.8643	High Similarity	NPC475856
0.8639	High Similarity	NPC193779
0.863	High Similarity	NPC87883
0.8623	High Similarity	NPC149008
0.8623	High Similarity	NPC283114
0.8623	High Similarity	NPC207702
0.8609	High Similarity	NPC178574
0.8609	High Similarity	NPC65591
0.8609	High Similarity	NPC475116
0.8609	High Similarity	NPC474606
0.86	High Similarity	NPC475756
0.86	High Similarity	NPC474975
0.8581	High Similarity	NPC295297
0.8581	High Similarity	NPC319749
0.8581	High Similarity	NPC191352
0.8581	High Similarity	NPC258322
0.8571	High Similarity	NPC470932
0.8562	High Similarity	NPC474288
0.8562	High Similarity	NPC301897
0.8562	High Similarity	NPC29727
0.8561	High Similarity	NPC153547
0.8553	High Similarity	NPC473425
0.8544	High Similarity	NPC471180
0.8543	High Similarity	NPC471154
0.8543	High Similarity	NPC272566
0.8542	High Similarity	NPC470962
0.8533	High Similarity	NPC473989
0.8531	High Similarity	NPC32189
0.8526	High Similarity	NPC280778
0.8516	High Similarity	NPC474770
0.8514	High Similarity	NPC213482
0.8514	High Similarity	NPC474054
0.8506	High Similarity	NPC19947
0.8506	High Similarity	NPC207584
0.8506	High Similarity	NPC181168
0.8506	High Similarity	NPC163527
0.8506	High Similarity	NPC115281
0.85	High Similarity	NPC178737
0.8487	Intermediate Similarity	NPC126405
0.8487	Intermediate Similarity	NPC217708
0.8487	Intermediate Similarity	NPC77237
0.8487	Intermediate Similarity	NPC308739
0.8487	Intermediate Similarity	NPC245948
0.8487	Intermediate Similarity	NPC53669
0.8487	Intermediate Similarity	NPC16791
0.8487	Intermediate Similarity	NPC477377
0.8487	Intermediate Similarity	NPC24562
0.8487	Intermediate Similarity	NPC297271
0.8477	Intermediate Similarity	NPC224472
0.8471	Intermediate Similarity	NPC475865
0.8467	Intermediate Similarity	NPC474965
0.8467	Intermediate Similarity	NPC174512
0.8467	Intermediate Similarity	NPC474347
0.8467	Intermediate Similarity	NPC125570
0.8467	Intermediate Similarity	NPC474393
0.8467	Intermediate Similarity	NPC477698
0.8467	Intermediate Similarity	NPC216223
0.8467	Intermediate Similarity	NPC477695
0.8467	Intermediate Similarity	NPC293757
0.8467	Intermediate Similarity	NPC145569
0.8467	Intermediate Similarity	NPC668
0.8456	Intermediate Similarity	NPC183083
0.8456	Intermediate Similarity	NPC137352
0.8452	Intermediate Similarity	NPC125713
0.8452	Intermediate Similarity	NPC474043
0.8442	Intermediate Similarity	NPC32373
0.8442	Intermediate Similarity	NPC237946
0.8442	Intermediate Similarity	NPC150227
0.8438	Intermediate Similarity	NPC477883
0.8431	Intermediate Similarity	NPC198461
0.8431	Intermediate Similarity	NPC30009
0.8431	Intermediate Similarity	NPC312763
0.8431	Intermediate Similarity	NPC103197
0.8421	Intermediate Similarity	NPC475229
0.8421	Intermediate Similarity	NPC477378
0.8414	Intermediate Similarity	NPC201404
0.8414	Intermediate Similarity	NPC290714
0.8414	Intermediate Similarity	NPC53722
0.8411	Intermediate Similarity	NPC477381
0.8411	Intermediate Similarity	NPC470916
0.8403	Intermediate Similarity	NPC11453
0.8403	Intermediate Similarity	NPC143895
0.8397	Intermediate Similarity	NPC470637
0.8397	Intermediate Similarity	NPC96593
0.8397	Intermediate Similarity	NPC63061
0.8389	Intermediate Similarity	NPC474446
0.8387	Intermediate Similarity	NPC190020
0.8387	Intermediate Similarity	NPC77679
0.8387	Intermediate Similarity	NPC84935
0.8385	Intermediate Similarity	NPC471181
0.838	Intermediate Similarity	NPC102256
0.8377	Intermediate Similarity	NPC79998
0.8377	Intermediate Similarity	NPC234730
0.8377	Intermediate Similarity	NPC476065
0.8377	Intermediate Similarity	NPC199926
0.8369	Intermediate Similarity	NPC470624
0.8369	Intermediate Similarity	NPC476399
0.8369	Intermediate Similarity	NPC237169
0.8367	Intermediate Similarity	NPC229172
0.8367	Intermediate Similarity	NPC230538
0.8367	Intermediate Similarity	NPC253481
0.8367	Intermediate Similarity	NPC253722
0.8367	Intermediate Similarity	NPC103637
0.8367	Intermediate Similarity	NPC31751
0.8367	Intermediate Similarity	NPC36531
0.8367	Intermediate Similarity	NPC46180
0.8365	Intermediate Similarity	NPC83049
0.8365	Intermediate Similarity	NPC118162
0.8365	Intermediate Similarity	NPC320471
0.8356	Intermediate Similarity	NPC103448
0.8356	Intermediate Similarity	NPC216434
0.8355	Intermediate Similarity	NPC164082
0.8355	Intermediate Similarity	NPC477379
0.8355	Intermediate Similarity	NPC477700
0.8354	Intermediate Similarity	NPC469475
0.8354	Intermediate Similarity	NPC469518
0.8345	Intermediate Similarity	NPC285725
0.8345	Intermediate Similarity	NPC50683
0.8345	Intermediate Similarity	NPC88297
0.8345	Intermediate Similarity	NPC186845
0.8345	Intermediate Similarity	NPC9891
0.8345	Intermediate Similarity	NPC112571
0.8344	Intermediate Similarity	NPC288149
0.8344	Intermediate Similarity	NPC239890

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 NPC18211 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	904
0.2-0.3	1682
0.3-0.4	2651
0.4-0.5	1884
0.5-0.6	1096
0.6-0.7	499
0.7-0.8	122
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8487	Intermediate Similarity	NPD37	Approved
0.8462	Intermediate Similarity	NPD7199	Phase 2
0.8442	Intermediate Similarity	NPD4967	Phase 2
0.8442	Intermediate Similarity	NPD4966	Approved
0.8442	Intermediate Similarity	NPD4965	Approved
0.8354	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6234	Discontinued
0.8158	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6232	Discontinued
0.805	Intermediate Similarity	NPD5494	Approved
0.8025	Intermediate Similarity	NPD7473	Discontinued
0.7975	Intermediate Similarity	NPD7228	Approved
0.795	Intermediate Similarity	NPD7229	Phase 3
0.7927	Intermediate Similarity	NPD5844	Phase 1
0.7911	Intermediate Similarity	NPD3817	Phase 2
0.7875	Intermediate Similarity	NPD919	Approved
0.7867	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD3882	Suspended
0.7848	Intermediate Similarity	NPD1465	Phase 2
0.7843	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2533	Approved
0.7792	Intermediate Similarity	NPD2534	Approved
0.7792	Intermediate Similarity	NPD2532	Approved
0.7791	Intermediate Similarity	NPD3926	Phase 2
0.7784	Intermediate Similarity	NPD7240	Approved
0.7736	Intermediate Similarity	NPD7819	Suspended
0.7733	Intermediate Similarity	NPD2438	Suspended
0.773	Intermediate Similarity	NPD3705	Approved
0.7714	Intermediate Similarity	NPD17	Approved
0.7683	Intermediate Similarity	NPD5242	Approved
0.7673	Intermediate Similarity	NPD1934	Approved
0.7667	Intermediate Similarity	NPD3748	Approved
0.7635	Intermediate Similarity	NPD2979	Phase 3
0.7628	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2801	Approved
0.7613	Intermediate Similarity	NPD6799	Approved
0.7606	Intermediate Similarity	NPD1281	Approved
0.7591	Intermediate Similarity	NPD5283	Phase 1
0.7584	Intermediate Similarity	NPD6355	Discontinued
0.7578	Intermediate Similarity	NPD5353	Approved
0.7564	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1247	Approved
0.7552	Intermediate Similarity	NPD1608	Approved
0.7551	Intermediate Similarity	NPD3027	Phase 3
0.7547	Intermediate Similarity	NPD6599	Discontinued
0.7545	Intermediate Similarity	NPD3818	Discontinued
0.7544	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3018	Phase 2
0.7532	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4110	Phase 3
0.7516	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD6099	Approved
0.7468	Intermediate Similarity	NPD1243	Approved
0.7468	Intermediate Similarity	NPD920	Approved
0.7467	Intermediate Similarity	NPD230	Phase 1
0.7448	Intermediate Similarity	NPD1283	Approved
0.7431	Intermediate Similarity	NPD2981	Phase 2
0.7419	Intermediate Similarity	NPD3750	Approved
0.7407	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4060	Phase 1
0.7399	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1651	Approved
0.7391	Intermediate Similarity	NPD6386	Approved
0.7391	Intermediate Similarity	NPD6385	Approved
0.7386	Intermediate Similarity	NPD2531	Phase 2
0.7379	Intermediate Similarity	NPD2982	Phase 2
0.7379	Intermediate Similarity	NPD2983	Phase 2
0.7378	Intermediate Similarity	NPD3749	Approved
0.7342	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6166	Phase 2
0.7321	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4628	Phase 3
0.7308	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3787	Discontinued
0.7297	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1613	Approved
0.7285	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3267	Approved
0.7279	Intermediate Similarity	NPD3266	Approved
0.7278	Intermediate Similarity	NPD1511	Approved
0.7273	Intermediate Similarity	NPD7075	Discontinued
0.7273	Intermediate Similarity	NPD5691	Approved
0.7267	Intermediate Similarity	NPD6798	Discontinued
0.7254	Intermediate Similarity	NPD5536	Phase 2
0.7251	Intermediate Similarity	NPD7074	Phase 3
0.7248	Intermediate Similarity	NPD4908	Phase 1
0.7248	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6801	Discontinued
0.7233	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD3146	Approved
0.7225	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8032	Phase 2
0.7208	Intermediate Similarity	NPD1510	Phase 2
0.7208	Intermediate Similarity	NPD7033	Discontinued
0.7202	Intermediate Similarity	NPD5710	Approved
0.7202	Intermediate Similarity	NPD5711	Approved
0.7193	Intermediate Similarity	NPD7054	Approved
0.7188	Intermediate Similarity	NPD1512	Approved
0.7178	Intermediate Similarity	NPD7411	Suspended
0.7178	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1240	Approved
0.7162	Intermediate Similarity	NPD2797	Approved
0.7153	Intermediate Similarity	NPD5585	Approved
0.7152	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3268	Approved
0.7152	Intermediate Similarity	NPD6190	Approved
0.7152	Intermediate Similarity	NPD1296	Phase 2
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7472	Approved
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6959	Discontinued
0.7134	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1933	Approved
0.7123	Intermediate Similarity	NPD1610	Phase 2
0.7117	Intermediate Similarity	NPD4380	Phase 2
0.7115	Intermediate Similarity	NPD5763	Approved
0.7115	Intermediate Similarity	NPD5762	Approved
0.7115	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7768	Phase 2
0.7086	Intermediate Similarity	NPD4625	Phase 3
0.7078	Intermediate Similarity	NPD1607	Approved
0.707	Intermediate Similarity	NPD2897	Discontinued
0.707	Intermediate Similarity	NPD1549	Phase 2
0.7063	Intermediate Similarity	NPD4357	Discontinued
0.7051	Intermediate Similarity	NPD2935	Discontinued
0.7051	Intermediate Similarity	NPD4476	Approved
0.7051	Intermediate Similarity	NPD3539	Phase 1
0.7051	Intermediate Similarity	NPD4477	Approved
0.7048	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5402	Approved
0.7039	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3764	Approved
0.7035	Intermediate Similarity	NPD3751	Discontinued
0.7029	Intermediate Similarity	NPD7808	Phase 3
0.7027	Intermediate Similarity	NPD5005	Approved
0.7027	Intermediate Similarity	NPD5006	Approved
0.702	Intermediate Similarity	NPD6832	Phase 2
0.7018	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD447	Suspended
0.7012	Intermediate Similarity	NPD6875	Approved
0.7012	Intermediate Similarity	NPD6876	Approved
0.7011	Intermediate Similarity	NPD6797	Phase 2
0.7007	Intermediate Similarity	NPD1611	Approved
0.7006	Intermediate Similarity	NPD3540	Phase 1
0.7006	Intermediate Similarity	NPD6002	Phase 3
0.7006	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6004	Phase 3
0.7006	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6005	Phase 3
0.7	Intermediate Similarity	NPD7124	Phase 2
0.7	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6233	Phase 2
0.6989	Remote Similarity	NPD7680	Approved
0.6987	Remote Similarity	NPD2799	Discontinued
0.6986	Remote Similarity	NPD4626	Approved
0.6986	Remote Similarity	NPD1778	Approved
0.6983	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6746	Phase 2
0.698	Remote Similarity	NPD1876	Approved
0.6975	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7095	Approved
0.6971	Remote Similarity	NPD7685	Pre-registration
0.6971	Remote Similarity	NPD6559	Discontinued
0.6971	Remote Similarity	NPD7251	Discontinued
0.6966	Remote Similarity	NPD8434	Phase 2
0.6964	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4005	Discontinued
0.6951	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD943	Approved
0.6946	Remote Similarity	NPD5978	Approved
0.6946	Remote Similarity	NPD5977	Approved
0.6943	Remote Similarity	NPD1551	Phase 2
0.6933	Remote Similarity	NPD5403	Approved
0.6933	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5110	Phase 2
0.6928	Remote Similarity	NPD5111	Phase 2
0.6928	Remote Similarity	NPD5109	Approved
0.6923	Remote Similarity	NPD6111	Discontinued
0.6919	Remote Similarity	NPD4481	Phase 3
0.6919	Remote Similarity	NPD2403	Approved
0.6918	Remote Similarity	NPD2654	Approved
0.6918	Remote Similarity	NPD6674	Discontinued
0.6918	Remote Similarity	NPD2800	Approved
0.6914	Remote Similarity	NPD5401	Approved
0.6913	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4359	Approved
0.6913	Remote Similarity	NPD4749	Approved
0.6909	Remote Similarity	NPD7028	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