NPASS Compound

Structure

NPC155924 OpenBabel07101719252D 29 33 0 0 1 0 0 0 0 0999 V2000 -4.1315 1.3894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5963 -0.2579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2784 2.3164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8910 -0.7128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4373 1.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6231 1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7570 1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8226 2.8698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.7653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6942 0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6231 -1.7128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0250 -0.2128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7570 -1.2128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1590 0.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4891 -0.2128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3884 0.7202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6231 0.2872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4891 -1.2128 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8910 1.2872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4158 1.9563 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8910 0.2872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0250 1.7872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7570 -0.2128 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1590 1.2872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3551 -1.7128 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 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 5 10 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 19 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 26 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 0 0 0 0 16 27 1 0 0 0 0 16 29 1 0 0 0 0 18 22 1 0 0 0 0 18 25 2 0 0 0 0 19 26 1 1 0 0 0 20 28 1 1 0 0 0 21 7 1 6 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 27 1 1 0 0 0 23 26 1 1 0 0 0 24 27 1 1 0 0 0 25 29 1 0 0 0 0 26 4 1 1 0 0 0 27 14 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.33
Volume:	447.71
LogP:	6.956
LogD:	5.555
LogS:	-6.278
# Rotatable Bonds:	3
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.569
Synthetic Accessibility Score:	5.114
Fsp3:	0.926
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.708
MDCK Permeability:	1.1632597306743264e-05
Pgp-inhibitor:	0.789
Pgp-substrate:	0.935
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.302
Plasma Protein Binding (PPB):	93.83196258544922%
Volume Distribution (VD):	1.457
Pgp-substrate:	1.5634284019470215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.485
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.294
CYP2C19-substrate:	0.757
CYP2C9-inhibitor:	0.604
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.247
CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.933
CYP3A4-substrate:	0.41

ADMET: Excretion

Clearance (CL):	16.225
Half-life (T1/2):	0.047

ADMET: Toxicity

hERG Blockers:	0.98
Human Hepatotoxicity (H-HT):	0.3
Drug-inuced Liver Injury (DILI):	0.849
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.97
Carcinogencity:	0.343
Eye Corrosion:	0.607
Eye Irritation:	0.496
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC155924

Natural Product ID:	NPC155924
*Common Name:**	FWDWUWPIWNWLFQ-ZWQSCVCHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FWDWUWPIWNWLFQ-ZWQSCVCHSA-N
Standard InCHI:	InChI=1S/C27H44O2/c1-17(2)5-10-25-18(3)22-8-9-24-21-7-6-19-15-20(28)11-13-26(19,4)23(21)12-14-27(22,24)16-29-25/h17,19-24,28H,5-16H2,1-4H3/t19-,20-,21+,22+,23-,24-,26-,27-/m0/s1
SMILES:	CC(CCC1=C(C)[C@@H]2[C@@]3(CO1)CC[C@H]1[C@H]([C@@H]3CC2)CC[C@@H]2[C@]1(C)CC[C@@H](C2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463892
PubChem CID:	21577173
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003027] 3-hydroxysteroids [CHEMONTID:0003233] 3-beta-hydroxysteroids

*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
NPO32762	axinella cf. bidderi	Species	Axinellidae	Eukaryota	n.a.	Indian Ocean	n.a.	PMID[12542339]
NPO32762	axinella cf. bidderi	Species	Axinellidae	Eukaryota	n.a.	Indian Ocean	n.a.	PMID[15043442]

☑ 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
GI50	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT858	Cell Line	LNCaP	Homo sapiens	GI50	=	2.88	ug.mL-1	PMID[497447]
NPT114	Cell Line	LoVo	Homo sapiens	GI50	=	8.29	ug.mL-1	PMID[497447]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	6.66	ug.mL-1	PMID[497447]

☑ 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 NPC155924 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	180
0.1-0.2	1747
0.2-0.3	7839
0.3-0.4	16214
0.4-0.5	6676
0.5-0.6	5057
0.6-0.7	3963
0.7-0.8	917
0.8-0.85	93
0.85-0.9	10
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9103	High Similarity	NPC5985
0.859	High Similarity	NPC285761
0.859	High Similarity	NPC167037
0.859	High Similarity	NPC244385
0.859	High Similarity	NPC138621
0.859	High Similarity	NPC6978
0.8571	High Similarity	NPC237460
0.8481	Intermediate Similarity	NPC273410
0.8481	Intermediate Similarity	NPC80530
0.8442	Intermediate Similarity	NPC231256
0.8442	Intermediate Similarity	NPC471723
0.8442	Intermediate Similarity	NPC240235
0.8442	Intermediate Similarity	NPC257347
0.8442	Intermediate Similarity	NPC178383
0.8442	Intermediate Similarity	NPC212879
0.8442	Intermediate Similarity	NPC141071
0.8442	Intermediate Similarity	NPC104387
0.8421	Intermediate Similarity	NPC201373
0.8375	Intermediate Similarity	NPC322313
0.8375	Intermediate Similarity	NPC236237
0.8375	Intermediate Similarity	NPC102253
0.8375	Intermediate Similarity	NPC13554
0.8354	Intermediate Similarity	NPC85346
0.8354	Intermediate Similarity	NPC65897
0.8354	Intermediate Similarity	NPC302041
0.8333	Intermediate Similarity	NPC78067
0.8333	Intermediate Similarity	NPC129165
0.8333	Intermediate Similarity	NPC14112
0.8333	Intermediate Similarity	NPC321016
0.8333	Intermediate Similarity	NPC107059
0.8333	Intermediate Similarity	NPC73875
0.8333	Intermediate Similarity	NPC86305
0.8333	Intermediate Similarity	NPC189883
0.8333	Intermediate Similarity	NPC134330
0.8333	Intermediate Similarity	NPC278091
0.8333	Intermediate Similarity	NPC93662
0.8333	Intermediate Similarity	NPC321381
0.8312	Intermediate Similarity	NPC25511
0.8312	Intermediate Similarity	NPC62657
0.8312	Intermediate Similarity	NPC192638
0.8289	Intermediate Similarity	NPC111234
0.825	Intermediate Similarity	NPC30986
0.825	Intermediate Similarity	NPC209430
0.825	Intermediate Similarity	NPC1319
0.8228	Intermediate Similarity	NPC248830
0.8228	Intermediate Similarity	NPC214570
0.8228	Intermediate Similarity	NPC198968
0.8228	Intermediate Similarity	NPC119355
0.8228	Intermediate Similarity	NPC202540
0.8228	Intermediate Similarity	NPC155986
0.8228	Intermediate Similarity	NPC318495
0.8228	Intermediate Similarity	NPC212241
0.8205	Intermediate Similarity	NPC121744
0.8205	Intermediate Similarity	NPC118508
0.8205	Intermediate Similarity	NPC162742
0.8205	Intermediate Similarity	NPC3403
0.8205	Intermediate Similarity	NPC136188
0.8205	Intermediate Similarity	NPC230301
0.8205	Intermediate Similarity	NPC304309
0.8205	Intermediate Similarity	NPC28657
0.8205	Intermediate Similarity	NPC322353
0.8205	Intermediate Similarity	NPC70982
0.8205	Intermediate Similarity	NPC185536
0.8205	Intermediate Similarity	NPC22105
0.8205	Intermediate Similarity	NPC288035
0.8205	Intermediate Similarity	NPC285893
0.8205	Intermediate Similarity	NPC230704
0.8205	Intermediate Similarity	NPC134847
0.8193	Intermediate Similarity	NPC209802
0.8193	Intermediate Similarity	NPC474047
0.8182	Intermediate Similarity	NPC195489
0.8171	Intermediate Similarity	NPC470049
0.8171	Intermediate Similarity	NPC218616
0.8171	Intermediate Similarity	NPC20853
0.8171	Intermediate Similarity	NPC248886
0.8171	Intermediate Similarity	NPC296701
0.8158	Intermediate Similarity	NPC45296
0.8148	Intermediate Similarity	NPC236112
0.8125	Intermediate Similarity	NPC473943
0.8125	Intermediate Similarity	NPC474216
0.8125	Intermediate Similarity	NPC275910
0.8125	Intermediate Similarity	NPC102708
0.8125	Intermediate Similarity	NPC312328
0.8125	Intermediate Similarity	NPC477522
0.8125	Intermediate Similarity	NPC42853
0.8125	Intermediate Similarity	NPC87604
0.8101	Intermediate Similarity	NPC240604
0.8101	Intermediate Similarity	NPC46160
0.8101	Intermediate Similarity	NPC202642
0.8101	Intermediate Similarity	NPC300324
0.8101	Intermediate Similarity	NPC470362
0.8101	Intermediate Similarity	NPC113733
0.8101	Intermediate Similarity	NPC91573
0.8095	Intermediate Similarity	NPC16350
0.8095	Intermediate Similarity	NPC308041
0.8077	Intermediate Similarity	NPC469533
0.8077	Intermediate Similarity	NPC49168
0.8077	Intermediate Similarity	NPC5046
0.8077	Intermediate Similarity	NPC196358
0.8077	Intermediate Similarity	NPC469593
0.8077	Intermediate Similarity	NPC308440
0.8077	Intermediate Similarity	NPC472503
0.8077	Intermediate Similarity	NPC469534
0.8077	Intermediate Similarity	NPC145552
0.8077	Intermediate Similarity	NPC100334
0.8077	Intermediate Similarity	NPC254509
0.8072	Intermediate Similarity	NPC207013
0.8072	Intermediate Similarity	NPC5280
0.8072	Intermediate Similarity	NPC110778
0.8072	Intermediate Similarity	NPC132635
0.8072	Intermediate Similarity	NPC470558
0.8072	Intermediate Similarity	NPC113978
0.8072	Intermediate Similarity	NPC477818
0.8049	Intermediate Similarity	NPC474531
0.8049	Intermediate Similarity	NPC116202
0.8049	Intermediate Similarity	NPC474683
0.8049	Intermediate Similarity	NPC7505
0.8049	Intermediate Similarity	NPC474759
0.8049	Intermediate Similarity	NPC82986
0.8049	Intermediate Similarity	NPC474731
0.8049	Intermediate Similarity	NPC70927
0.8049	Intermediate Similarity	NPC474752
0.8025	Intermediate Similarity	NPC116119
0.8025	Intermediate Similarity	NPC143182
0.8025	Intermediate Similarity	NPC475727
0.8025	Intermediate Similarity	NPC49599
0.8025	Intermediate Similarity	NPC109546
0.8025	Intermediate Similarity	NPC80297
0.8025	Intermediate Similarity	NPC472463
0.8025	Intermediate Similarity	NPC49627
0.8025	Intermediate Similarity	NPC84694
0.8025	Intermediate Similarity	NPC328714
0.8025	Intermediate Similarity	NPC28862
0.8025	Intermediate Similarity	NPC47982
0.8025	Intermediate Similarity	NPC81306
0.8025	Intermediate Similarity	NPC472742
0.8023	Intermediate Similarity	NPC471952
0.8	Intermediate Similarity	NPC157996
0.8	Intermediate Similarity	NPC474970
0.8	Intermediate Similarity	NPC34177
0.8	Intermediate Similarity	NPC331618
0.8	Intermediate Similarity	NPC472805
0.8	Intermediate Similarity	NPC24277
0.8	Intermediate Similarity	NPC40394
0.8	Intermediate Similarity	NPC125399
0.8	Intermediate Similarity	NPC34019
0.8	Intermediate Similarity	NPC90979
0.8	Intermediate Similarity	NPC257191
0.8	Intermediate Similarity	NPC101475
0.7976	Intermediate Similarity	NPC470077
0.7975	Intermediate Similarity	NPC200243
0.7975	Intermediate Similarity	NPC103822
0.7975	Intermediate Similarity	NPC34700
0.7975	Intermediate Similarity	NPC138374
0.7952	Intermediate Similarity	NPC30166
0.7949	Intermediate Similarity	NPC474140
0.7945	Intermediate Similarity	NPC114891
0.7931	Intermediate Similarity	NPC74258
0.7927	Intermediate Similarity	NPC164840
0.7927	Intermediate Similarity	NPC234193
0.7927	Intermediate Similarity	NPC22403
0.7927	Intermediate Similarity	NPC26117
0.7927	Intermediate Similarity	NPC206735
0.7927	Intermediate Similarity	NPC241290
0.7927	Intermediate Similarity	NPC209944
0.7927	Intermediate Similarity	NPC475679
0.7922	Intermediate Similarity	NPC282454
0.7901	Intermediate Similarity	NPC477514
0.7901	Intermediate Similarity	NPC300499
0.7901	Intermediate Similarity	NPC98386
0.7901	Intermediate Similarity	NPC230295
0.7901	Intermediate Similarity	NPC307965
0.7901	Intermediate Similarity	NPC470396
0.7901	Intermediate Similarity	NPC474989
0.7901	Intermediate Similarity	NPC205455
0.7901	Intermediate Similarity	NPC301707
0.7901	Intermediate Similarity	NPC158662
0.7901	Intermediate Similarity	NPC99168
0.7901	Intermediate Similarity	NPC22955
0.7901	Intermediate Similarity	NPC76931
0.7901	Intermediate Similarity	NPC196753
0.7901	Intermediate Similarity	NPC477817
0.7901	Intermediate Similarity	NPC253807
0.7901	Intermediate Similarity	NPC72507
0.7901	Intermediate Similarity	NPC186191
0.7901	Intermediate Similarity	NPC31828
0.7901	Intermediate Similarity	NPC472342
0.7901	Intermediate Similarity	NPC477819
0.7901	Intermediate Similarity	NPC18603
0.7895	Intermediate Similarity	NPC160209
0.7882	Intermediate Similarity	NPC474349
0.7882	Intermediate Similarity	NPC474189
0.7875	Intermediate Similarity	NPC38141
0.7875	Intermediate Similarity	NPC122418
0.7875	Intermediate Similarity	NPC244488
0.7875	Intermediate Similarity	NPC290598
0.7875	Intermediate Similarity	NPC265328
0.7875	Intermediate Similarity	NPC27765
0.7875	Intermediate Similarity	NPC120098
0.7875	Intermediate Similarity	NPC30590

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 NPC155924 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	2049
0.2-0.3	4392
0.3-0.4	1849
0.4-0.5	302
0.5-0.6	170
0.6-0.7	177
0.7-0.8	41
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8375	Intermediate Similarity	NPD7525	Registered
0.8205	Intermediate Similarity	NPD7339	Approved
0.8205	Intermediate Similarity	NPD6942	Approved
0.8025	Intermediate Similarity	NPD7645	Phase 2
0.7875	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4748	Discontinued
0.7625	Intermediate Similarity	NPD6924	Approved
0.7625	Intermediate Similarity	NPD6926	Approved
0.7558	Intermediate Similarity	NPD4786	Approved
0.7471	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6933	Approved
0.7375	Intermediate Similarity	NPD4243	Approved
0.7375	Intermediate Similarity	NPD7150	Approved
0.7375	Intermediate Similarity	NPD7151	Approved
0.7375	Intermediate Similarity	NPD7152	Approved
0.7342	Intermediate Similarity	NPD6923	Approved
0.7342	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6922	Approved
0.7333	Intermediate Similarity	NPD5328	Approved
0.7326	Intermediate Similarity	NPD3667	Approved
0.725	Intermediate Similarity	NPD7143	Approved
0.725	Intermediate Similarity	NPD7144	Approved
0.725	Intermediate Similarity	NPD4787	Phase 1
0.7241	Intermediate Similarity	NPD6695	Phase 3
0.7195	Intermediate Similarity	NPD4784	Approved
0.7195	Intermediate Similarity	NPD4785	Approved
0.7191	Intermediate Similarity	NPD3618	Phase 1
0.7176	Intermediate Similarity	NPD6929	Approved
0.7174	Intermediate Similarity	NPD8034	Phase 2
0.7174	Intermediate Similarity	NPD8035	Phase 2
0.7174	Intermediate Similarity	NPD6079	Approved
0.716	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6399	Phase 3
0.7093	Intermediate Similarity	NPD7509	Discontinued
0.7093	Intermediate Similarity	NPD6930	Phase 2
0.7093	Intermediate Similarity	NPD6931	Approved
0.7093	Intermediate Similarity	NPD6928	Phase 2
0.7083	Intermediate Similarity	NPD7638	Approved
0.7045	Intermediate Similarity	NPD4788	Approved
0.701	Intermediate Similarity	NPD7640	Approved
0.701	Intermediate Similarity	NPD7639	Approved
0.6988	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3133	Approved
0.6966	Remote Similarity	NPD3665	Phase 1
0.6966	Remote Similarity	NPD3666	Approved
0.6941	Remote Similarity	NPD6925	Approved
0.6941	Remote Similarity	NPD6932	Approved
0.6941	Remote Similarity	NPD5776	Phase 2
0.6923	Remote Similarity	NPD7524	Approved
0.6923	Remote Similarity	NPD7750	Discontinued
0.6915	Remote Similarity	NPD4202	Approved
0.6914	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4190	Phase 3
0.6905	Remote Similarity	NPD5275	Approved
0.6869	Remote Similarity	NPD7632	Discontinued
0.686	Remote Similarity	NPD7145	Approved
0.686	Remote Similarity	NPD3617	Approved
0.6848	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7748	Approved
0.6824	Remote Similarity	NPD6117	Approved
0.6809	Remote Similarity	NPD7515	Phase 2
0.6782	Remote Similarity	NPD4195	Approved
0.6782	Remote Similarity	NPD6683	Phase 2
0.6768	Remote Similarity	NPD4159	Approved
0.6744	Remote Similarity	NPD6116	Phase 1
0.6705	Remote Similarity	NPD7514	Phase 3
0.6703	Remote Similarity	NPD6893	Approved
0.6701	Remote Similarity	NPD4697	Phase 3
0.6701	Remote Similarity	NPD5222	Approved
0.6701	Remote Similarity	NPD5221	Approved
0.6701	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD6118	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6114	Approved
0.6667	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6115	Approved
0.6667	Remote Similarity	NPD6697	Approved
0.6633	Remote Similarity	NPD5173	Approved
0.6633	Remote Similarity	NPD7902	Approved
0.6633	Remote Similarity	NPD4755	Approved
0.6633	Remote Similarity	NPD6084	Phase 2
0.6633	Remote Similarity	NPD6083	Phase 2
0.6632	Remote Similarity	NPD7087	Discontinued
0.663	Remote Similarity	NPD5279	Phase 3
0.663	Remote Similarity	NPD6684	Approved
0.663	Remote Similarity	NPD7334	Approved
0.663	Remote Similarity	NPD7146	Approved
0.663	Remote Similarity	NPD6409	Approved
0.663	Remote Similarity	NPD5330	Approved
0.663	Remote Similarity	NPD7521	Approved
0.6629	Remote Similarity	NPD6902	Approved
0.6627	Remote Similarity	NPD4789	Approved
0.6627	Remote Similarity	NPD4244	Approved
0.6627	Remote Similarity	NPD4245	Approved
0.6596	Remote Similarity	NPD4753	Phase 2
0.6596	Remote Similarity	NPD6051	Approved
0.6593	Remote Similarity	NPD3668	Phase 3
0.6585	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5360	Phase 3
0.6556	Remote Similarity	NPD4223	Phase 3
0.6556	Remote Similarity	NPD4221	Approved
0.6538	Remote Similarity	NPD6881	Approved
0.6538	Remote Similarity	NPD6899	Approved
0.6538	Remote Similarity	NPD7320	Approved
0.6522	Remote Similarity	NPD5329	Approved
0.6517	Remote Similarity	NPD7332	Phase 2
0.6512	Remote Similarity	NPD8264	Approved
0.6512	Remote Similarity	NPD3703	Phase 2
0.6506	Remote Similarity	NPD3698	Phase 2
0.65	Remote Similarity	NPD5286	Approved
0.65	Remote Similarity	NPD5285	Approved
0.65	Remote Similarity	NPD4696	Approved
0.65	Remote Similarity	NPD4700	Approved
0.6489	Remote Similarity	NPD6903	Approved
0.6489	Remote Similarity	NPD5737	Approved
0.6489	Remote Similarity	NPD6672	Approved
0.6476	Remote Similarity	NPD6372	Approved
0.6476	Remote Similarity	NPD6373	Approved
0.6444	Remote Similarity	NPD4139	Approved
0.6444	Remote Similarity	NPD6898	Phase 1
0.6444	Remote Similarity	NPD4692	Approved
0.6442	Remote Similarity	NPD5697	Approved
0.6442	Remote Similarity	NPD5701	Approved
0.6436	Remote Similarity	NPD5223	Approved
0.642	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7290	Approved
0.6415	Remote Similarity	NPD6883	Approved
0.6415	Remote Similarity	NPD7102	Approved
0.6413	Remote Similarity	NPD4197	Approved
0.64	Remote Similarity	NPD5290	Discontinued
0.6381	Remote Similarity	NPD6011	Approved
0.6373	Remote Similarity	NPD4633	Approved
0.6373	Remote Similarity	NPD5211	Phase 2
0.6373	Remote Similarity	NPD5225	Approved
0.6373	Remote Similarity	NPD5224	Approved
0.6373	Remote Similarity	NPD5226	Approved
0.6364	Remote Similarity	NPD7115	Discovery
0.6355	Remote Similarity	NPD6847	Approved
0.6355	Remote Similarity	NPD6649	Approved
0.6355	Remote Similarity	NPD6869	Approved
0.6355	Remote Similarity	NPD6617	Approved
0.6355	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6650	Approved
0.6355	Remote Similarity	NPD8130	Phase 1
0.6327	Remote Similarity	NPD7900	Approved
0.6327	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6014	Approved
0.6321	Remote Similarity	NPD6012	Approved
0.6321	Remote Similarity	NPD6013	Approved
0.6311	Remote Similarity	NPD5175	Approved
0.6311	Remote Similarity	NPD5174	Approved
0.6311	Remote Similarity	NPD4754	Approved
0.6306	Remote Similarity	NPD7328	Approved
0.6306	Remote Similarity	NPD7327	Approved
0.6296	Remote Similarity	NPD6882	Approved
0.6296	Remote Similarity	NPD8297	Approved
0.6292	Remote Similarity	NPD3671	Phase 1
0.6289	Remote Similarity	NPD7637	Suspended
0.6286	Remote Similarity	NPD6412	Phase 2
0.6283	Remote Similarity	NPD7503	Approved
0.6277	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4688	Approved
0.6277	Remote Similarity	NPD4690	Approved
0.6277	Remote Similarity	NPD5205	Approved
0.6277	Remote Similarity	NPD4138	Approved
0.6277	Remote Similarity	NPD4693	Phase 3
0.6277	Remote Similarity	NPD6098	Approved
0.6277	Remote Similarity	NPD4689	Approved
0.6263	Remote Similarity	NPD4629	Approved
0.6263	Remote Similarity	NPD5210	Approved
0.6263	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD7516	Approved
0.6238	Remote Similarity	NPD5696	Approved
0.6224	Remote Similarity	NPD8171	Discontinued
0.6195	Remote Similarity	NPD8377	Approved
0.6195	Remote Similarity	NPD8294	Approved
0.619	Remote Similarity	NPD4768	Approved
0.619	Remote Similarity	NPD4767	Approved
0.619	Remote Similarity	NPD6705	Phase 1
0.6163	Remote Similarity	NPD4758	Discontinued
0.6163	Remote Similarity	NPD5777	Approved
0.6146	Remote Similarity	NPD4723	Approved
0.6146	Remote Similarity	NPD4722	Approved
0.614	Remote Similarity	NPD8335	Approved
0.614	Remote Similarity	NPD8033	Approved
0.614	Remote Similarity	NPD8379	Approved
0.614	Remote Similarity	NPD8378	Approved
0.614	Remote Similarity	NPD8296	Approved
0.614	Remote Similarity	NPD8380	Approved
0.6136	Remote Similarity	NPD3702	Approved
0.6126	Remote Similarity	NPD6868	Approved
0.6105	Remote Similarity	NPD5690	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