NPASS Compound

Structure

NPC188896 OpenBabel07101718202D 24 26 0 0 1 0 0 0 0 0999 V2000 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 -0.5000 -0.8660 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 -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 -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 -2.5981 1.5000 0.0000 C 0 0 1 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 0 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 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 5 6 1 0 0 0 0 5 16 1 0 0 0 0 6 19 1 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 13 1 0 0 0 0 10 15 2 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 13 23 1 1 0 0 0 14 20 1 1 0 0 0 15 17 1 0 0 0 0 15 20 1 0 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 24 1 0 0 0 0 20 11 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.08
Volume:	382.318
LogP:	4.663
LogD:	3.98
LogS:	-5.385
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.444
Synthetic Accessibility Score:	5.142
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:	-4.433
MDCK Permeability:	1.8457965779816732e-05
Pgp-inhibitor:	0.282
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.095
30% Bioavailability (F30%):	0.769

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.704
Plasma Protein Binding (PPB):	86.08335876464844%
Volume Distribution (VD):	1.281
Pgp-substrate:	12.326811790466309%

ADMET: Metabolism

CYP1A2-inhibitor:	0.442
CYP1A2-substrate:	0.654
CYP2C19-inhibitor:	0.268
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.703
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.113
CYP3A4-inhibitor:	0.84
CYP3A4-substrate:	0.653

ADMET: Excretion

Clearance (CL):	10.203
Half-life (T1/2):	0.048

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.286
AMES Toxicity:	0.284
Rat Oral Acute Toxicity:	0.909
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.503
Carcinogencity:	0.878
Eye Corrosion:	0.782
Eye Irritation:	0.067
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC188896

Natural Product ID:	NPC188896
*Common Name:**	2S-Hydroxyisobromosphaerol
IUPAC Name:	(1S,3S,4bS,5R,8S,8aS,10aS)-8-bromo-10a-(bromomethyl)-5,8a-dimethyl-1-propan-2-yl-2,3,4b,6,7,8,9,10-octahydro-1H-phenanthrene-3,5-diol
Synonyms:	2S-Hydroxyisobromosphaerol
Standard InCHIKey:	YZPAZPZQHZGBFE-FSUCBALESA-N
Standard InCHI:	InChI=1S/C20H32Br2O2/c1-12(2)14-9-13(23)10-15-17-18(3,7-8-20(14,15)11-21)16(22)5-6-19(17,4)24/h10,12-14,16-17,23-24H,5-9,11H2,1-4H3/t13-,14-,16-,17-,18+,19+,20-/m0/s1
SMILES:	CC(C)[C@@H]1C[C@@H](C=C2[C@H]3[C@](C)(CC[C@]12CBr)[C@H](CC[C@@]3(C)O)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476352
PubChem CID:	25018716
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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[568645]

☑ 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 NPC188896 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	210
0.1-0.2	1747
0.2-0.3	7121
0.3-0.4	17288
0.4-0.5	8075
0.5-0.6	5786
0.6-0.7	2058
0.7-0.8	381
0.8-0.85	23
0.85-0.9	4
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC131453
0.9101	High Similarity	NPC257510
0.9101	High Similarity	NPC299714
0.8791	High Similarity	NPC156912
0.875	High Similarity	NPC239453
0.875	High Similarity	NPC224552
0.8675	High Similarity	NPC129501
0.8495	Intermediate Similarity	NPC92231
0.8495	Intermediate Similarity	NPC34732
0.8471	Intermediate Similarity	NPC311891
0.8434	Intermediate Similarity	NPC91594
0.8353	Intermediate Similarity	NPC113024
0.8295	Intermediate Similarity	NPC313115
0.8235	Intermediate Similarity	NPC476610
0.8214	Intermediate Similarity	NPC470758
0.8214	Intermediate Similarity	NPC470711
0.8111	Intermediate Similarity	NPC174273
0.8095	Intermediate Similarity	NPC265588
0.8095	Intermediate Similarity	NPC470749
0.8072	Intermediate Similarity	NPC476366
0.8072	Intermediate Similarity	NPC201048
0.8046	Intermediate Similarity	NPC476646
0.7976	Intermediate Similarity	NPC474946
0.7976	Intermediate Similarity	NPC35397
0.7976	Intermediate Similarity	NPC32832
0.7955	Intermediate Similarity	NPC49964
0.7952	Intermediate Similarity	NPC476609
0.7931	Intermediate Similarity	NPC96362
0.7931	Intermediate Similarity	NPC295131
0.7927	Intermediate Similarity	NPC34834
0.7907	Intermediate Similarity	NPC476314
0.7907	Intermediate Similarity	NPC167891
0.7907	Intermediate Similarity	NPC83351
0.7857	Intermediate Similarity	NPC243342
0.7857	Intermediate Similarity	NPC477138
0.7841	Intermediate Similarity	NPC249423
0.7841	Intermediate Similarity	NPC264245
0.7831	Intermediate Similarity	NPC475077
0.7831	Intermediate Similarity	NPC167706
0.7831	Intermediate Similarity	NPC242001
0.7816	Intermediate Similarity	NPC143182
0.7816	Intermediate Similarity	NPC84694
0.7816	Intermediate Similarity	NPC209430
0.7816	Intermediate Similarity	NPC30986
0.7816	Intermediate Similarity	NPC81306
0.7816	Intermediate Similarity	NPC109546
0.7816	Intermediate Similarity	NPC291379
0.7816	Intermediate Similarity	NPC47982
0.7816	Intermediate Similarity	NPC28862
0.7802	Intermediate Similarity	NPC6391
0.7802	Intermediate Similarity	NPC261266
0.7791	Intermediate Similarity	NPC471798
0.7778	Intermediate Similarity	NPC205845
0.7765	Intermediate Similarity	NPC66566
0.7765	Intermediate Similarity	NPC477923
0.7765	Intermediate Similarity	NPC291503
0.7765	Intermediate Similarity	NPC476605
0.7753	Intermediate Similarity	NPC218616
0.7753	Intermediate Similarity	NPC101462
0.7753	Intermediate Similarity	NPC87489
0.7753	Intermediate Similarity	NPC296701
0.7742	Intermediate Similarity	NPC329643
0.7738	Intermediate Similarity	NPC265485
0.7738	Intermediate Similarity	NPC182717
0.7738	Intermediate Similarity	NPC471799
0.7738	Intermediate Similarity	NPC220939
0.7727	Intermediate Similarity	NPC234193
0.7727	Intermediate Similarity	NPC241290
0.7727	Intermediate Similarity	NPC164840
0.7727	Intermediate Similarity	NPC209944
0.7711	Intermediate Similarity	NPC145498
0.7701	Intermediate Similarity	NPC274750
0.7701	Intermediate Similarity	NPC22955
0.7701	Intermediate Similarity	NPC99168
0.7701	Intermediate Similarity	NPC474989
0.7701	Intermediate Similarity	NPC474216
0.7701	Intermediate Similarity	NPC215307
0.7701	Intermediate Similarity	NPC470396
0.7701	Intermediate Similarity	NPC11908
0.7692	Intermediate Similarity	NPC274448
0.7674	Intermediate Similarity	NPC247325
0.7674	Intermediate Similarity	NPC244488
0.7674	Intermediate Similarity	NPC61080
0.7674	Intermediate Similarity	NPC253190
0.7667	Intermediate Similarity	NPC317458
0.7667	Intermediate Similarity	NPC474634
0.7667	Intermediate Similarity	NPC475789
0.7647	Intermediate Similarity	NPC100334
0.7647	Intermediate Similarity	NPC237510
0.7647	Intermediate Similarity	NPC91858
0.7647	Intermediate Similarity	NPC471797
0.7647	Intermediate Similarity	NPC475793
0.7647	Intermediate Similarity	NPC306727
0.764	Intermediate Similarity	NPC47761
0.764	Intermediate Similarity	NPC23852
0.764	Intermediate Similarity	NPC209620
0.7619	Intermediate Similarity	NPC23954
0.7614	Intermediate Similarity	NPC53744
0.759	Intermediate Similarity	NPC476604
0.7586	Intermediate Similarity	NPC318495
0.7586	Intermediate Similarity	NPC90979
0.7586	Intermediate Similarity	NPC40394
0.7586	Intermediate Similarity	NPC34177
0.7586	Intermediate Similarity	NPC198968
0.7586	Intermediate Similarity	NPC155986
0.7586	Intermediate Similarity	NPC101475
0.7586	Intermediate Similarity	NPC130136
0.7586	Intermediate Similarity	NPC477924
0.7586	Intermediate Similarity	NPC157996
0.7586	Intermediate Similarity	NPC472805
0.7582	Intermediate Similarity	NPC238485
0.7582	Intermediate Similarity	NPC231310
0.7582	Intermediate Similarity	NPC185568
0.7582	Intermediate Similarity	NPC470077
0.7582	Intermediate Similarity	NPC474047
0.7561	Intermediate Similarity	NPC68703
0.7561	Intermediate Similarity	NPC69649
0.7561	Intermediate Similarity	NPC114651
0.7556	Intermediate Similarity	NPC470049
0.7556	Intermediate Similarity	NPC202389
0.7556	Intermediate Similarity	NPC189972
0.7556	Intermediate Similarity	NPC155521
0.7556	Intermediate Similarity	NPC304285
0.7556	Intermediate Similarity	NPC50964
0.7553	Intermediate Similarity	NPC470361
0.7527	Intermediate Similarity	NPC149224
0.75	Intermediate Similarity	NPC318390
0.75	Intermediate Similarity	NPC230295
0.75	Intermediate Similarity	NPC196753
0.75	Intermediate Similarity	NPC285761
0.75	Intermediate Similarity	NPC300499
0.75	Intermediate Similarity	NPC157257
0.75	Intermediate Similarity	NPC92801
0.75	Intermediate Similarity	NPC473943
0.75	Intermediate Similarity	NPC158662
0.75	Intermediate Similarity	NPC253807
0.75	Intermediate Similarity	NPC266511
0.75	Intermediate Similarity	NPC98386
0.75	Intermediate Similarity	NPC470360
0.75	Intermediate Similarity	NPC275910
0.7474	Intermediate Similarity	NPC11216
0.7474	Intermediate Similarity	NPC3345
0.7474	Intermediate Similarity	NPC329596
0.7474	Intermediate Similarity	NPC295668
0.7474	Intermediate Similarity	NPC291484
0.7474	Intermediate Similarity	NPC80561
0.7474	Intermediate Similarity	NPC204188
0.7473	Intermediate Similarity	NPC82623
0.7473	Intermediate Similarity	NPC470384
0.7471	Intermediate Similarity	NPC321016
0.7471	Intermediate Similarity	NPC106364
0.7471	Intermediate Similarity	NPC189883
0.7471	Intermediate Similarity	NPC122418
0.7471	Intermediate Similarity	NPC240604
0.7471	Intermediate Similarity	NPC265328
0.7471	Intermediate Similarity	NPC476606
0.7471	Intermediate Similarity	NPC290598
0.7471	Intermediate Similarity	NPC274079
0.7471	Intermediate Similarity	NPC27765
0.7471	Intermediate Similarity	NPC300324
0.7471	Intermediate Similarity	NPC476607
0.7471	Intermediate Similarity	NPC107059
0.7471	Intermediate Similarity	NPC106432
0.7471	Intermediate Similarity	NPC477925
0.7471	Intermediate Similarity	NPC321381
0.7471	Intermediate Similarity	NPC120098
0.7471	Intermediate Similarity	NPC30590
0.747	Intermediate Similarity	NPC208999
0.747	Intermediate Similarity	NPC96484
0.7451	Intermediate Similarity	NPC133921
0.7447	Intermediate Similarity	NPC133588
0.7447	Intermediate Similarity	NPC474668
0.7444	Intermediate Similarity	NPC474731
0.7444	Intermediate Similarity	NPC474752
0.7444	Intermediate Similarity	NPC474759
0.7444	Intermediate Similarity	NPC474531
0.7444	Intermediate Similarity	NPC159148
0.7444	Intermediate Similarity	NPC474683
0.7444	Intermediate Similarity	NPC7505
0.7444	Intermediate Similarity	NPC82986
0.7442	Intermediate Similarity	NPC469534
0.7442	Intermediate Similarity	NPC469593
0.7442	Intermediate Similarity	NPC469533
0.7439	Intermediate Similarity	NPC202017
0.7419	Intermediate Similarity	NPC299068
0.7419	Intermediate Similarity	NPC470955
0.7419	Intermediate Similarity	NPC293287
0.7419	Intermediate Similarity	NPC152808
0.7419	Intermediate Similarity	NPC82979
0.7416	Intermediate Similarity	NPC80530
0.7416	Intermediate Similarity	NPC476603
0.7416	Intermediate Similarity	NPC31330
0.7416	Intermediate Similarity	NPC328714
0.7416	Intermediate Similarity	NPC1319
0.7416	Intermediate Similarity	NPC472463
0.7416	Intermediate Similarity	NPC273410
0.7412	Intermediate Similarity	NPC110799
0.7412	Intermediate Similarity	NPC164022
0.7412	Intermediate Similarity	NPC477792
0.7396	Intermediate Similarity	NPC41554

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 NPC188896 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	2059
0.2-0.3	4282
0.3-0.4	1908
0.4-0.5	395
0.5-0.6	216
0.6-0.7	79
0.7-0.8	7
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
0.7416	Intermediate Similarity	NPD7645	Phase 2
0.7356	Intermediate Similarity	NPD6942	Approved
0.7356	Intermediate Similarity	NPD7339	Approved
0.7333	Intermediate Similarity	NPD7525	Registered
0.7273	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD8264	Approved
0.7158	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6924	Approved
0.7045	Intermediate Similarity	NPD6926	Approved
0.6957	Remote Similarity	NPD6930	Phase 2
0.6957	Remote Similarity	NPD6931	Approved
0.6923	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6933	Approved
0.6854	Remote Similarity	NPD4785	Approved
0.6854	Remote Similarity	NPD4784	Approved
0.6848	Remote Similarity	NPD6929	Approved
0.6842	Remote Similarity	NPD4786	Approved
0.6818	Remote Similarity	NPD4243	Approved
0.6809	Remote Similarity	NPD3667	Approved
0.6774	Remote Similarity	NPD7509	Discontinued
0.6774	Remote Similarity	NPD7514	Phase 3
0.6774	Remote Similarity	NPD7332	Phase 2
0.6747	Remote Similarity	NPD368	Approved
0.6737	Remote Similarity	NPD6695	Phase 3
0.6701	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5328	Approved
0.663	Remote Similarity	NPD6925	Approved
0.663	Remote Similarity	NPD5776	Phase 2
0.6604	Remote Similarity	NPD7632	Discontinued
0.6598	Remote Similarity	NPD6893	Approved
0.6596	Remote Similarity	NPD4748	Discontinued
0.6591	Remote Similarity	NPD6922	Approved
0.6591	Remote Similarity	NPD6923	Approved
0.6559	Remote Similarity	NPD7145	Approved
0.6535	Remote Similarity	NPD7515	Phase 2
0.6535	Remote Similarity	NPD6079	Approved
0.6526	Remote Similarity	NPD6898	Phase 1
0.6526	Remote Similarity	NPD6902	Approved
0.6517	Remote Similarity	NPD7143	Approved
0.6517	Remote Similarity	NPD7144	Approved
0.6495	Remote Similarity	NPD3666	Approved
0.6495	Remote Similarity	NPD3665	Phase 1
0.6495	Remote Similarity	NPD3133	Approved
0.6471	Remote Similarity	NPD4202	Approved
0.6465	Remote Similarity	NPD7524	Approved
0.6465	Remote Similarity	NPD7750	Discontinued
0.6452	Remote Similarity	NPD6932	Approved
0.6444	Remote Similarity	NPD7150	Approved
0.6444	Remote Similarity	NPD7152	Approved
0.6444	Remote Similarity	NPD7151	Approved
0.6415	Remote Similarity	NPD7639	Approved
0.6415	Remote Similarity	NPD7640	Approved
0.6413	Remote Similarity	NPD4190	Phase 3
0.6413	Remote Similarity	NPD5275	Approved
0.6364	Remote Similarity	NPD4519	Discontinued
0.6364	Remote Similarity	NPD4623	Approved
0.6321	Remote Similarity	NPD7638	Approved
0.6316	Remote Similarity	NPD4195	Approved
0.6316	Remote Similarity	NPD6683	Phase 2
0.6296	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD7748	Approved
0.6226	Remote Similarity	NPD4755	Approved
0.622	Remote Similarity	NPD342	Phase 1
0.6214	Remote Similarity	NPD7087	Discontinued
0.6182	Remote Similarity	NPD5141	Approved
0.6176	Remote Similarity	NPD4753	Phase 2
0.6176	Remote Similarity	NPD6051	Approved
0.6168	Remote Similarity	NPD4225	Approved
0.6162	Remote Similarity	NPD3668	Phase 3
0.6154	Remote Similarity	NPD6399	Phase 3
0.6132	Remote Similarity	NPD5222	Approved
0.6132	Remote Similarity	NPD4697	Phase 3
0.6132	Remote Similarity	NPD5221	Approved
0.6132	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4223	Phase 3
0.6122	Remote Similarity	NPD4221	Approved
0.6111	Remote Similarity	NPD5286	Approved
0.6111	Remote Similarity	NPD4700	Approved
0.6111	Remote Similarity	NPD4696	Approved
0.6111	Remote Similarity	NPD5285	Approved
0.61	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5329	Approved
0.6082	Remote Similarity	NPD4695	Discontinued
0.6075	Remote Similarity	NPD7902	Approved
0.6075	Remote Similarity	NPD5173	Approved
0.6068	Remote Similarity	NPD6274	Approved
0.6055	Remote Similarity	NPD5223	Approved
0.6055	Remote Similarity	NPD4159	Approved
0.604	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5279	Phase 3
0.6019	Remote Similarity	NPD5290	Discontinued
0.6017	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD4197	Approved
0.6	Remote Similarity	NPD5224	Approved
0.5982	Remote Similarity	NPD5739	Approved
0.5982	Remote Similarity	NPD7128	Approved
0.5982	Remote Similarity	NPD6675	Approved
0.5982	Remote Similarity	NPD6402	Approved
0.5946	Remote Similarity	NPD4754	Approved
0.5946	Remote Similarity	NPD5175	Approved
0.5946	Remote Similarity	NPD5174	Approved
0.5941	Remote Similarity	NPD1696	Phase 3
0.5926	Remote Similarity	NPD6083	Phase 2
0.5926	Remote Similarity	NPD6084	Phase 2
0.5905	Remote Similarity	NPD7637	Suspended
0.5905	Remote Similarity	NPD6411	Approved
0.59	Remote Similarity	NPD4788	Approved
0.5888	Remote Similarity	NPD4629	Approved
0.5888	Remote Similarity	NPD5210	Approved
0.5882	Remote Similarity	NPD6409	Approved
0.5882	Remote Similarity	NPD7521	Approved
0.5882	Remote Similarity	NPD4689	Approved
0.5882	Remote Similarity	NPD4688	Approved
0.5882	Remote Similarity	NPD5205	Approved
0.5882	Remote Similarity	NPD4138	Approved
0.5882	Remote Similarity	NPD7334	Approved
0.5882	Remote Similarity	NPD4690	Approved
0.5882	Remote Similarity	NPD4693	Phase 3
0.5882	Remote Similarity	NPD5330	Approved
0.5882	Remote Similarity	NPD7146	Approved
0.5882	Remote Similarity	NPD6684	Approved
0.5877	Remote Similarity	NPD7320	Approved
0.5877	Remote Similarity	NPD6899	Approved
0.5877	Remote Similarity	NPD6881	Approved
0.5876	Remote Similarity	NPD3671	Phase 1
0.587	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD4732	Discontinued
0.5849	Remote Similarity	NPD5778	Approved
0.5849	Remote Similarity	NPD5779	Approved
0.5841	Remote Similarity	NPD4768	Approved
0.5841	Remote Similarity	NPD4767	Approved
0.5826	Remote Similarity	NPD6373	Approved
0.5826	Remote Similarity	NPD6372	Approved
0.581	Remote Similarity	NPD7136	Phase 2
0.5794	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7900	Approved
0.5789	Remote Similarity	NPD5701	Approved
0.5789	Remote Similarity	NPD5697	Approved
0.5776	Remote Similarity	NPD7102	Approved
0.5776	Remote Similarity	NPD7290	Approved
0.5776	Remote Similarity	NPD6883	Approved
0.5769	Remote Similarity	NPD4722	Approved
0.5769	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD4723	Approved
0.5769	Remote Similarity	NPD6903	Approved
0.5765	Remote Similarity	NPD4219	Approved
0.5739	Remote Similarity	NPD4730	Approved
0.5739	Remote Similarity	NPD6011	Approved
0.5739	Remote Similarity	NPD4729	Approved
0.5739	Remote Similarity	NPD5128	Approved
0.5728	Remote Similarity	NPD4694	Approved
0.5728	Remote Similarity	NPD5280	Approved
0.5728	Remote Similarity	NPD5690	Phase 2
0.5726	Remote Similarity	NPD6649	Approved
0.5726	Remote Similarity	NPD6617	Approved
0.5726	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8130	Phase 1
0.5726	Remote Similarity	NPD6869	Approved
0.5726	Remote Similarity	NPD6847	Approved
0.5726	Remote Similarity	NPD6650	Approved
0.5714	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6101	Approved
0.5714	Remote Similarity	NPD3617	Approved
0.569	Remote Similarity	NPD6014	Approved
0.569	Remote Similarity	NPD6013	Approved
0.569	Remote Similarity	NPD6012	Approved
0.5686	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD6882	Approved
0.5678	Remote Similarity	NPD8297	Approved
0.5673	Remote Similarity	NPD3573	Approved
0.5641	Remote Similarity	NPD5250	Approved
0.5641	Remote Similarity	NPD5169	Approved
0.5641	Remote Similarity	NPD5249	Phase 3
0.5641	Remote Similarity	NPD5251	Approved
0.5641	Remote Similarity	NPD5248	Approved
0.5641	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD4634	Approved
0.5641	Remote Similarity	NPD5247	Approved
0.5641	Remote Similarity	NPD5135	Approved
0.5638	Remote Similarity	NPD4787	Phase 1
0.5625	Remote Similarity	NPD5344	Discontinued
0.5619	Remote Similarity	NPD6672	Approved
0.5619	Remote Similarity	NPD5737	Approved
0.5607	Remote Similarity	NPD8034	Phase 2
0.5607	Remote Similarity	NPD8035	Phase 2
0.5603	Remote Similarity	NPD5168	Approved
0.56	Remote Similarity	NPD4820	Approved
0.56	Remote Similarity	NPD4819	Approved
0.56	Remote Similarity	NPD4821	Approved
0.56	Remote Similarity	NPD4822	Approved
0.56	Remote Similarity	NPD8259	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data