NPASS Compound

Structure

NPC129501 OpenBabel07101718182D 23 25 0 0 1 0 0 0 0 0999 V2000 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 5 6 1 0 0 0 0 5 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 14 20 1 1 0 0 0 15 17 1 0 0 0 0 15 20 1 6 0 0 0 16 18 1 1 0 0 0 16 22 1 0 0 0 0 17 18 1 1 0 0 0 17 19 1 0 0 0 0 18 3 1 1 0 0 0 19 4 1 6 0 0 0 19 23 1 0 0 0 0 20 12 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.08
Volume:	373.528
LogP:	6.053
LogD:	4.471
LogS:	-5.947
# Rotatable Bonds:	2
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	5.224
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.35
MDCK Permeability:	2.075441625493113e-05
Pgp-inhibitor:	0.048
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.039
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.857

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.553
Plasma Protein Binding (PPB):	96.4668960571289%
Volume Distribution (VD):	1.295
Pgp-substrate:	3.7343688011169434%

ADMET: Metabolism

CYP1A2-inhibitor:	0.683
CYP1A2-substrate:	0.327
CYP2C19-inhibitor:	0.449
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.796
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.121
CYP2D6-substrate:	0.227
CYP3A4-inhibitor:	0.88
CYP3A4-substrate:	0.533

ADMET: Excretion

Clearance (CL):	7.348
Half-life (T1/2):	0.037

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.251
Drug-inuced Liver Injury (DILI):	0.853
AMES Toxicity:	0.101
Rat Oral Acute Toxicity:	0.628
Maximum Recommended Daily Dose:	0.073
Skin Sensitization:	0.928
Carcinogencity:	0.634
Eye Corrosion:	0.97
Eye Irritation:	0.485
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: NPC129501

Natural Product ID:	NPC129501
*Common Name:**	Bromosphaerol
IUPAC Name:	(1S,4R,4aS,4bS,8S,8aS,10aS)-1-bromo-8a-(bromomethyl)-4,10a-dimethyl-8-propan-2-yl-2,3,4a,4b,7,8,9,10-octahydro-1H-phenanthren-4-ol
Synonyms:	Bromosphaerol
Standard InCHIKey:	ZMLPTEUWDOZWSU-INCXTXFYSA-N
Standard InCHI:	InChI=1S/C20H32Br2O/c1-13(2)14-6-5-7-15-17-18(3,10-11-20(14,15)12-21)16(22)8-9-19(17,4)23/h5,7,13-17,23H,6,8-12H2,1-4H3/t14-,15-,16-,17-,18+,19+,20-/m0/s1
SMILES:	BrC[C@@]12CC[C@]3([C@H]([C@@H]2C=CC[C@H]1C(C)C)[C@](C)(O)CC[C@@H]3Br)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL599536
PubChem CID:	14565462
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO29354	Sphaerococcus coronopifolius	Species	Sphaerococcaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520219]
NPO29354	Sphaerococcus coronopifolius	Species	Sphaerococcaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18597527]
NPO29354	Sphaerococcus coronopifolius	Species	Sphaerococcaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20045651]
NPO29354	Sphaerococcus coronopifolius	Species	Sphaerococcaceae	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	6

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	35000.0	nM	PMID[557987]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	34000.0	nM	PMID[557987]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	30000.0	nM	PMID[557987]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	23000.0	nM	PMID[557987]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	30000.0	nM	PMID[557987]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	28000.0	nM	PMID[557987]

☑ 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 NPC129501 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	219
0.1-0.2	2346
0.2-0.3	13994
0.3-0.4	14034
0.4-0.5	7193
0.5-0.6	3879
0.6-0.7	922
0.7-0.8	96
0.8-0.85	8
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8902	High Similarity	NPC131453
0.8795	High Similarity	NPC239453
0.8795	High Similarity	NPC224552
0.8675	High Similarity	NPC188896
0.8571	High Similarity	NPC329643
0.8481	Intermediate Similarity	NPC476610
0.8333	Intermediate Similarity	NPC61080
0.8289	Intermediate Similarity	NPC475077
0.8202	Intermediate Similarity	NPC156912
0.8111	Intermediate Similarity	NPC34732
0.8111	Intermediate Similarity	NPC92231
0.809	Intermediate Similarity	NPC257510
0.809	Intermediate Similarity	NPC299714
0.7895	Intermediate Similarity	NPC94192
0.7882	Intermediate Similarity	NPC313115
0.7792	Intermediate Similarity	NPC476431
0.7792	Intermediate Similarity	NPC476604
0.7722	Intermediate Similarity	NPC182717
0.7701	Intermediate Similarity	NPC174273
0.7692	Intermediate Similarity	NPC475728
0.7632	Intermediate Similarity	NPC279434
0.7532	Intermediate Similarity	NPC197805
0.7531	Intermediate Similarity	NPC474946
0.7531	Intermediate Similarity	NPC35397
0.75	Intermediate Similarity	NPC64123
0.747	Intermediate Similarity	NPC215307
0.747	Intermediate Similarity	NPC274750
0.7468	Intermediate Similarity	NPC145498
0.7423	Intermediate Similarity	NPC133921
0.7412	Intermediate Similarity	NPC311891
0.7407	Intermediate Similarity	NPC243342
0.7407	Intermediate Similarity	NPC91858
0.7407	Intermediate Similarity	NPC475793
0.7407	Intermediate Similarity	NPC100334
0.7407	Intermediate Similarity	NPC237510
0.7407	Intermediate Similarity	NPC477138
0.7403	Intermediate Similarity	NPC286669
0.7403	Intermediate Similarity	NPC222366
0.7403	Intermediate Similarity	NPC476039
0.7375	Intermediate Similarity	NPC167706
0.7375	Intermediate Similarity	NPC110799
0.7375	Intermediate Similarity	NPC242001
0.7349	Intermediate Similarity	NPC91594
0.7349	Intermediate Similarity	NPC471798
0.7333	Intermediate Similarity	NPC79576
0.7333	Intermediate Similarity	NPC194208
0.7333	Intermediate Similarity	NPC282694
0.7317	Intermediate Similarity	NPC291503
0.7294	Intermediate Similarity	NPC113024
0.7284	Intermediate Similarity	NPC471799
0.7284	Intermediate Similarity	NPC476609
0.7229	Intermediate Similarity	NPC470749
0.7229	Intermediate Similarity	NPC30590
0.7229	Intermediate Similarity	NPC189883
0.7229	Intermediate Similarity	NPC106432
0.7229	Intermediate Similarity	NPC120098
0.7229	Intermediate Similarity	NPC122418
0.7229	Intermediate Similarity	NPC265328
0.7229	Intermediate Similarity	NPC30575
0.7229	Intermediate Similarity	NPC290598
0.7229	Intermediate Similarity	NPC265588
0.7229	Intermediate Similarity	NPC134330
0.7229	Intermediate Similarity	NPC27765
0.7229	Intermediate Similarity	NPC129165
0.7215	Intermediate Similarity	NPC2648
0.7215	Intermediate Similarity	NPC32055
0.7195	Intermediate Similarity	NPC476366
0.7195	Intermediate Similarity	NPC22134
0.7195	Intermediate Similarity	NPC471797
0.7195	Intermediate Similarity	NPC201048
0.7176	Intermediate Similarity	NPC291379
0.7162	Intermediate Similarity	NPC474769
0.7162	Intermediate Similarity	NPC189290
0.7143	Intermediate Similarity	NPC130136
0.7143	Intermediate Similarity	NPC157996
0.7143	Intermediate Similarity	NPC90979
0.7143	Intermediate Similarity	NPC34177
0.7143	Intermediate Similarity	NPC472805
0.7143	Intermediate Similarity	NPC101475
0.7143	Intermediate Similarity	NPC470758
0.7143	Intermediate Similarity	NPC470711
0.7143	Intermediate Similarity	NPC40394
0.7125	Intermediate Similarity	NPC210323
0.7108	Intermediate Similarity	NPC471723
0.7108	Intermediate Similarity	NPC476605
0.7108	Intermediate Similarity	NPC477923
0.7108	Intermediate Similarity	NPC32832
0.7108	Intermediate Similarity	NPC141071
0.7108	Intermediate Similarity	NPC66566
0.7108	Intermediate Similarity	NPC138374
0.7108	Intermediate Similarity	NPC257347
0.7108	Intermediate Similarity	NPC34700
0.7105	Intermediate Similarity	NPC41160
0.7089	Intermediate Similarity	NPC88454
0.7089	Intermediate Similarity	NPC117607
0.7089	Intermediate Similarity	NPC101307
0.7079	Intermediate Similarity	NPC33663
0.7059	Intermediate Similarity	NPC98386
0.7059	Intermediate Similarity	NPC253807
0.7059	Intermediate Similarity	NPC474989
0.7059	Intermediate Similarity	NPC158662
0.7059	Intermediate Similarity	NPC285761
0.7059	Intermediate Similarity	NPC230295
0.7059	Intermediate Similarity	NPC22955
0.7059	Intermediate Similarity	NPC196753
0.7059	Intermediate Similarity	NPC470396
0.7059	Intermediate Similarity	NPC11908
0.7059	Intermediate Similarity	NPC99168
0.7059	Intermediate Similarity	NPC300499
0.7051	Intermediate Similarity	NPC163678
0.7045	Intermediate Similarity	NPC473592
0.7024	Intermediate Similarity	NPC202642
0.7024	Intermediate Similarity	NPC474231
0.7024	Intermediate Similarity	NPC470362
0.7024	Intermediate Similarity	NPC476607
0.7024	Intermediate Similarity	NPC113733
0.7024	Intermediate Similarity	NPC46160
0.7024	Intermediate Similarity	NPC240604
0.7024	Intermediate Similarity	NPC237460
0.7024	Intermediate Similarity	NPC300324
0.7024	Intermediate Similarity	NPC106364
0.7024	Intermediate Similarity	NPC476606
0.7013	Intermediate Similarity	NPC81615
0.7013	Intermediate Similarity	NPC174956
0.7011	Intermediate Similarity	NPC476646
0.7011	Intermediate Similarity	NPC249423
0.7	Intermediate Similarity	NPC208999
0.7	Intermediate Similarity	NPC216460
0.6977	Remote Similarity	NPC53744
0.6977	Remote Similarity	NPC31330
0.6977	Remote Similarity	NPC80530
0.6977	Remote Similarity	NPC273410
0.6977	Remote Similarity	NPC1319
0.6966	Remote Similarity	NPC470077
0.6962	Remote Similarity	NPC149680
0.6951	Remote Similarity	NPC164022
0.6941	Remote Similarity	NPC477924
0.6941	Remote Similarity	NPC214570
0.6941	Remote Similarity	NPC155986
0.6941	Remote Similarity	NPC476608
0.6941	Remote Similarity	NPC198968
0.6941	Remote Similarity	NPC318495
0.6941	Remote Similarity	NPC132542
0.6932	Remote Similarity	NPC218616
0.6932	Remote Similarity	NPC30166
0.6932	Remote Similarity	NPC49964
0.6932	Remote Similarity	NPC87489
0.6932	Remote Similarity	NPC296701
0.6923	Remote Similarity	NPC225415
0.6905	Remote Similarity	NPC28657
0.6905	Remote Similarity	NPC288035
0.6905	Remote Similarity	NPC121744
0.6905	Remote Similarity	NPC22105
0.6905	Remote Similarity	NPC230301
0.6905	Remote Similarity	NPC285893
0.6905	Remote Similarity	NPC304309
0.6905	Remote Similarity	NPC118508
0.6905	Remote Similarity	NPC134847
0.6905	Remote Similarity	NPC322353
0.6905	Remote Similarity	NPC476424
0.6905	Remote Similarity	NPC162742
0.6905	Remote Similarity	NPC136188
0.6897	Remote Similarity	NPC164840
0.6897	Remote Similarity	NPC96362
0.6897	Remote Similarity	NPC236237
0.6897	Remote Similarity	NPC13554
0.6897	Remote Similarity	NPC476809
0.6897	Remote Similarity	NPC469637
0.6897	Remote Similarity	NPC295131
0.6897	Remote Similarity	NPC102253
0.6897	Remote Similarity	NPC209944
0.6897	Remote Similarity	NPC236112
0.6897	Remote Similarity	NPC322313
0.6897	Remote Similarity	NPC287749
0.6897	Remote Similarity	NPC241290
0.6892	Remote Similarity	NPC39068
0.6892	Remote Similarity	NPC264779
0.6892	Remote Similarity	NPC179024
0.6889	Remote Similarity	NPC470360
0.6889	Remote Similarity	NPC318390
0.6867	Remote Similarity	NPC68443
0.686	Remote Similarity	NPC72507
0.686	Remote Similarity	NPC65897
0.686	Remote Similarity	NPC167037
0.686	Remote Similarity	NPC83351
0.686	Remote Similarity	NPC318136
0.686	Remote Similarity	NPC186191
0.686	Remote Similarity	NPC6978
0.686	Remote Similarity	NPC148977
0.686	Remote Similarity	NPC85346
0.686	Remote Similarity	NPC302041
0.686	Remote Similarity	NPC76931
0.686	Remote Similarity	NPC312328
0.686	Remote Similarity	NPC205455
0.686	Remote Similarity	NPC244385
0.686	Remote Similarity	NPC307965
0.686	Remote Similarity	NPC275910
0.686	Remote Similarity	NPC167891
0.686	Remote Similarity	NPC18603
0.686	Remote Similarity	NPC138621

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 NPC129501 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	2587
0.2-0.3	4398
0.3-0.4	1411
0.4-0.5	265
0.5-0.6	190
0.6-0.7	43
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7407	Intermediate Similarity	NPD4785	Approved
0.7407	Intermediate Similarity	NPD4784	Approved
0.7375	Intermediate Similarity	NPD4243	Approved
0.6977	Remote Similarity	NPD7645	Phase 2
0.6905	Remote Similarity	NPD7339	Approved
0.6905	Remote Similarity	NPD4190	Phase 3
0.6905	Remote Similarity	NPD5275	Approved
0.6905	Remote Similarity	NPD6942	Approved
0.6897	Remote Similarity	NPD7525	Registered
0.6782	Remote Similarity	NPD4195	Approved
0.6628	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6926	Approved
0.6395	Remote Similarity	NPD6924	Approved
0.6374	Remote Similarity	NPD4223	Phase 3
0.6374	Remote Similarity	NPD4221	Approved
0.6344	Remote Similarity	NPD5329	Approved
0.6289	Remote Similarity	NPD6079	Approved
0.6277	Remote Similarity	NPD3618	Phase 1
0.6277	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4519	Discontinued
0.6277	Remote Similarity	NPD4623	Approved
0.625	Remote Similarity	NPD5328	Approved
0.625	Remote Similarity	NPD6933	Approved
0.6237	Remote Similarity	NPD4197	Approved
0.6237	Remote Similarity	NPD4786	Approved
0.6235	Remote Similarity	NPD7144	Approved
0.6235	Remote Similarity	NPD7143	Approved
0.6196	Remote Similarity	NPD3667	Approved
0.6163	Remote Similarity	NPD7150	Approved
0.6163	Remote Similarity	NPD7151	Approved
0.6163	Remote Similarity	NPD7152	Approved
0.6154	Remote Similarity	NPD4695	Discontinued
0.6154	Remote Similarity	NPD7509	Discontinued
0.6136	Remote Similarity	NPD8264	Approved
0.6122	Remote Similarity	NPD7515	Phase 2
0.6118	Remote Similarity	NPD6922	Approved
0.6118	Remote Similarity	NPD6923	Approved
0.6105	Remote Similarity	NPD5690	Phase 2
0.6105	Remote Similarity	NPD4690	Approved
0.6105	Remote Similarity	NPD4138	Approved
0.6105	Remote Similarity	NPD4689	Approved
0.6105	Remote Similarity	NPD5205	Approved
0.6105	Remote Similarity	NPD4688	Approved
0.6105	Remote Similarity	NPD4693	Phase 3
0.6064	Remote Similarity	NPD3133	Approved
0.6064	Remote Similarity	NPD3666	Approved
0.6064	Remote Similarity	NPD3665	Phase 1
0.6061	Remote Similarity	NPD4202	Approved
0.6042	Remote Similarity	NPD3573	Approved
0.6042	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6932	Approved
0.6	Remote Similarity	NPD7748	Approved
0.5979	Remote Similarity	NPD4722	Approved
0.5979	Remote Similarity	NPD4723	Approved
0.5978	Remote Similarity	NPD6931	Approved
0.5978	Remote Similarity	NPD4748	Discontinued
0.5978	Remote Similarity	NPD6930	Phase 2
0.5938	Remote Similarity	NPD5280	Approved
0.5938	Remote Similarity	NPD4694	Approved
0.5934	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD3617	Approved
0.5918	Remote Similarity	NPD4753	Phase 2
0.5882	Remote Similarity	NPD5222	Approved
0.5882	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5221	Approved
0.587	Remote Similarity	NPD6929	Approved
0.5865	Remote Similarity	NPD5285	Approved
0.5865	Remote Similarity	NPD5286	Approved
0.5865	Remote Similarity	NPD4696	Approved
0.5825	Remote Similarity	NPD5173	Approved
0.5825	Remote Similarity	NPD7902	Approved
0.5825	Remote Similarity	NPD4755	Approved
0.581	Remote Similarity	NPD5223	Approved
0.5806	Remote Similarity	NPD7332	Phase 2
0.5806	Remote Similarity	NPD7514	Phase 3
0.58	Remote Similarity	NPD5281	Approved
0.58	Remote Similarity	NPD5284	Approved
0.5789	Remote Similarity	NPD6695	Phase 3
0.5784	Remote Similarity	NPD4629	Approved
0.5784	Remote Similarity	NPD5210	Approved
0.5773	Remote Similarity	NPD6098	Approved
0.5769	Remote Similarity	NPD5290	Discontinued
0.5761	Remote Similarity	NPD7145	Approved
0.5758	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD5226	Approved
0.5755	Remote Similarity	NPD5211	Phase 2
0.5755	Remote Similarity	NPD4633	Approved
0.5755	Remote Similarity	NPD5224	Approved
0.5755	Remote Similarity	NPD5225	Approved
0.5755	Remote Similarity	NPD7632	Discontinued
0.5745	Remote Similarity	NPD4692	Approved
0.5745	Remote Similarity	NPD4139	Approved
0.5743	Remote Similarity	NPD6399	Phase 3
0.5729	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD3668	Phase 3
0.5728	Remote Similarity	NPD4697	Phase 3
0.5714	Remote Similarity	NPD4700	Approved
0.5702	Remote Similarity	NPD6274	Approved
0.5701	Remote Similarity	NPD5174	Approved
0.5701	Remote Similarity	NPD5175	Approved
0.5699	Remote Similarity	NPD6683	Phase 2
0.5673	Remote Similarity	NPD6084	Phase 2
0.5673	Remote Similarity	NPD6083	Phase 2
0.567	Remote Similarity	NPD6893	Approved
0.567	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD368	Approved
0.5652	Remote Similarity	NPD5776	Phase 2
0.5652	Remote Similarity	NPD6925	Approved
0.5648	Remote Similarity	NPD5141	Approved
0.5636	Remote Similarity	NPD6899	Approved
0.5636	Remote Similarity	NPD6881	Approved
0.5632	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4788	Approved
0.5619	Remote Similarity	NPD7638	Approved
0.5612	Remote Similarity	NPD5330	Approved
0.5612	Remote Similarity	NPD7521	Approved
0.5612	Remote Similarity	NPD7334	Approved
0.5612	Remote Similarity	NPD5279	Phase 3
0.5612	Remote Similarity	NPD7146	Approved
0.5612	Remote Similarity	NPD6684	Approved
0.5612	Remote Similarity	NPD6409	Approved
0.56	Remote Similarity	NPD6080	Approved
0.56	Remote Similarity	NPD6051	Approved
0.56	Remote Similarity	NPD6673	Approved
0.56	Remote Similarity	NPD6904	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