NPASS Compound

Structure

NPC224552 OpenBabel07101718282D 24 26 0 0 1 0 0 0 0 0999 V2000 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 -0.5000 -0.8660 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 -3.4641 -1.0000 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 2.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 -2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 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 12 1 0 0 0 0 2 12 1 0 0 0 0 5 6 1 0 0 0 0 5 7 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 13 20 1 1 0 0 0 14 17 1 0 0 0 0 14 20 1 6 0 0 0 15 18 1 1 0 0 0 15 22 1 0 0 0 0 16 19 1 1 0 0 0 16 23 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:	5.501
LogD:	4.058
LogS:	-4.421
# 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:	0.451
Synthetic Accessibility Score:	5.391
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:	-4.56
MDCK Permeability:	3.210295835742727e-05
Pgp-inhibitor:	0.042
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.047
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.896

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.833
Plasma Protein Binding (PPB):	95.39380645751953%
Volume Distribution (VD):	1.298
Pgp-substrate:	6.307151794433594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.495
CYP1A2-substrate:	0.27
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.775
CYP2C9-inhibitor:	0.384
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.221
CYP3A4-inhibitor:	0.779
CYP3A4-substrate:	0.452

ADMET: Excretion

Clearance (CL):	9.954
Half-life (T1/2):	0.042

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.316
Drug-inuced Liver Injury (DILI):	0.578
AMES Toxicity:	0.136
Rat Oral Acute Toxicity:	0.336
Maximum Recommended Daily Dose:	0.134
Skin Sensitization:	0.807
Carcinogencity:	0.704
Eye Corrosion:	0.964
Eye Irritation:	0.241
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC224552

Natural Product ID:	NPC224552
*Common Name:**	12R-Hydroxy-Bromosphaerol
IUPAC Name:	(1S,3R,4S,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-phenanthrene-3,4-diol
Synonyms:	12R-Hydroxy-Bromosphaerol
Standard InCHIKey:	XQZDHNLVPFXQTQ-SDFFAQHVSA-N
Standard InCHI:	InChI=1S/C20H32Br2O2/c1-12(2)13-6-5-7-14-17-18(3,8-9-20(13,14)11-21)15(22)10-16(23)19(17,4)24/h5,7,12-17,23-24H,6,8-11H2,1-4H3/t13-,14-,15-,16+,17-,18+,19+,20-/m0/s1
SMILES:	CC(C)[C@@H]1CC=C[C@H]2[C@H]3[C@](C)(CC[C@]12CBr)[C@H](C[C@H]([C@@]3(C)O)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL604390
PubChem CID:	46232318
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	=	28000.0	nM	PMID[572116]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	29000.0	nM	PMID[572116]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	26000.0	nM	PMID[572116]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	26000.0	nM	PMID[572116]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	25000.0	nM	PMID[572116]

☑ 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 NPC224552 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	218
0.1-0.2	1984
0.2-0.3	8710
0.3-0.4	17441
0.4-0.5	7067
0.5-0.6	5506
0.6-0.7	1517
0.7-0.8	238
0.8-0.85	3
0.85-0.9	6
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC239453
0.9326	High Similarity	NPC156912
0.9222	High Similarity	NPC34732
0.9222	High Similarity	NPC92231
0.9213	High Similarity	NPC299714
0.9213	High Similarity	NPC257510
0.9059	High Similarity	NPC313115
0.8966	High Similarity	NPC131453
0.8851	High Similarity	NPC174273
0.8795	High Similarity	NPC129501
0.875	High Similarity	NPC188896
0.8454	Intermediate Similarity	NPC133921
0.7882	Intermediate Similarity	NPC477923
0.7882	Intermediate Similarity	NPC66566
0.7857	Intermediate Similarity	NPC182717
0.7849	Intermediate Similarity	NPC329643
0.7841	Intermediate Similarity	NPC287749
0.7841	Intermediate Similarity	NPC236112
0.7765	Intermediate Similarity	NPC237510
0.7765	Intermediate Similarity	NPC475793
0.7765	Intermediate Similarity	NPC243342
0.7765	Intermediate Similarity	NPC477138
0.7765	Intermediate Similarity	NPC91858
0.7753	Intermediate Similarity	NPC311891
0.7753	Intermediate Similarity	NPC474531
0.7738	Intermediate Similarity	NPC167706
0.7727	Intermediate Similarity	NPC476610
0.7701	Intermediate Similarity	NPC471798
0.7701	Intermediate Similarity	NPC477924
0.7701	Intermediate Similarity	NPC130136
0.7674	Intermediate Similarity	NPC476605
0.7674	Intermediate Similarity	NPC35397
0.7674	Intermediate Similarity	NPC291503
0.7674	Intermediate Similarity	NPC474946
0.7667	Intermediate Similarity	NPC30166
0.7667	Intermediate Similarity	NPC47763
0.7647	Intermediate Similarity	NPC471799
0.764	Intermediate Similarity	NPC13554
0.764	Intermediate Similarity	NPC113024
0.7614	Intermediate Similarity	NPC83351
0.7614	Intermediate Similarity	NPC167891
0.7614	Intermediate Similarity	NPC215307
0.7614	Intermediate Similarity	NPC274750
0.7586	Intermediate Similarity	NPC477925
0.7586	Intermediate Similarity	NPC106432
0.7586	Intermediate Similarity	NPC61080
0.7586	Intermediate Similarity	NPC274079
0.7586	Intermediate Similarity	NPC265588
0.7582	Intermediate Similarity	NPC159168
0.7582	Intermediate Similarity	NPC207013
0.7582	Intermediate Similarity	NPC253402
0.7558	Intermediate Similarity	NPC471797
0.7558	Intermediate Similarity	NPC100334
0.7553	Intermediate Similarity	NPC133588
0.7529	Intermediate Similarity	NPC242992
0.7529	Intermediate Similarity	NPC242001
0.7529	Intermediate Similarity	NPC110799
0.7528	Intermediate Similarity	NPC291379
0.7528	Intermediate Similarity	NPC328714
0.7527	Intermediate Similarity	NPC94462
0.75	Intermediate Similarity	NPC238992
0.75	Intermediate Similarity	NPC101475
0.75	Intermediate Similarity	NPC470711
0.75	Intermediate Similarity	NPC157996
0.75	Intermediate Similarity	NPC34177
0.75	Intermediate Similarity	NPC90979
0.75	Intermediate Similarity	NPC40394
0.75	Intermediate Similarity	NPC470758
0.75	Intermediate Similarity	NPC210323
0.75	Intermediate Similarity	NPC472805
0.75	Intermediate Similarity	NPC91594
0.7442	Intermediate Similarity	NPC476609
0.7416	Intermediate Similarity	NPC22955
0.7416	Intermediate Similarity	NPC158662
0.7416	Intermediate Similarity	NPC470396
0.7416	Intermediate Similarity	NPC196753
0.7416	Intermediate Similarity	NPC98386
0.7416	Intermediate Similarity	NPC253807
0.7416	Intermediate Similarity	NPC300499
0.7416	Intermediate Similarity	NPC474989
0.7416	Intermediate Similarity	NPC230295
0.7416	Intermediate Similarity	NPC11908
0.7416	Intermediate Similarity	NPC99168
0.7416	Intermediate Similarity	NPC285761
0.7412	Intermediate Similarity	NPC145498
0.7391	Intermediate Similarity	NPC317458
0.7386	Intermediate Similarity	NPC134330
0.7386	Intermediate Similarity	NPC189883
0.7386	Intermediate Similarity	NPC27765
0.7386	Intermediate Similarity	NPC290598
0.7386	Intermediate Similarity	NPC476606
0.7386	Intermediate Similarity	NPC265328
0.7386	Intermediate Similarity	NPC129165
0.7386	Intermediate Similarity	NPC30590
0.7386	Intermediate Similarity	NPC120098
0.7386	Intermediate Similarity	NPC470749
0.7386	Intermediate Similarity	NPC122418
0.7381	Intermediate Similarity	NPC244790
0.7381	Intermediate Similarity	NPC2648
0.7363	Intermediate Similarity	NPC476646
0.7363	Intermediate Similarity	NPC249423
0.7363	Intermediate Similarity	NPC6707
0.7356	Intermediate Similarity	NPC201048
0.7356	Intermediate Similarity	NPC476366
0.734	Intermediate Similarity	NPC237344
0.734	Intermediate Similarity	NPC125399
0.7333	Intermediate Similarity	NPC53744
0.7333	Intermediate Similarity	NPC273410
0.7333	Intermediate Similarity	NPC1319
0.7333	Intermediate Similarity	NPC80530
0.7326	Intermediate Similarity	NPC475077
0.7326	Intermediate Similarity	NPC164022
0.7326	Intermediate Similarity	NPC471268
0.7326	Intermediate Similarity	NPC471271
0.7312	Intermediate Similarity	NPC470077
0.7303	Intermediate Similarity	NPC318495
0.7303	Intermediate Similarity	NPC198968
0.7303	Intermediate Similarity	NPC214570
0.7303	Intermediate Similarity	NPC155986
0.7292	Intermediate Similarity	NPC109744
0.7283	Intermediate Similarity	NPC49964
0.7283	Intermediate Similarity	NPC218616
0.7283	Intermediate Similarity	NPC296701
0.7283	Intermediate Similarity	NPC87489
0.7273	Intermediate Similarity	NPC257347
0.7273	Intermediate Similarity	NPC141071
0.7273	Intermediate Similarity	NPC471723
0.7273	Intermediate Similarity	NPC138374
0.7273	Intermediate Similarity	NPC34700
0.7263	Intermediate Similarity	NPC186145
0.7263	Intermediate Similarity	NPC189777
0.7263	Intermediate Similarity	NPC470620
0.7263	Intermediate Similarity	NPC474657
0.7262	Intermediate Similarity	NPC197805
0.7253	Intermediate Similarity	NPC96362
0.7253	Intermediate Similarity	NPC102253
0.7253	Intermediate Similarity	NPC322313
0.7253	Intermediate Similarity	NPC295131
0.7253	Intermediate Similarity	NPC164840
0.7253	Intermediate Similarity	NPC236237
0.7253	Intermediate Similarity	NPC209944
0.7253	Intermediate Similarity	NPC241290
0.7253	Intermediate Similarity	NPC22403
0.7241	Intermediate Similarity	NPC68443
0.7234	Intermediate Similarity	NPC470360
0.7234	Intermediate Similarity	NPC318390
0.7222	Intermediate Similarity	NPC138621
0.7222	Intermediate Similarity	NPC244385
0.7222	Intermediate Similarity	NPC6978
0.7222	Intermediate Similarity	NPC148977
0.7222	Intermediate Similarity	NPC167037
0.7222	Intermediate Similarity	NPC72507
0.7222	Intermediate Similarity	NPC275910
0.7216	Intermediate Similarity	NPC473956
0.7216	Intermediate Similarity	NPC3345
0.7216	Intermediate Similarity	NPC475751
0.7216	Intermediate Similarity	NPC80561
0.7216	Intermediate Similarity	NPC291484
0.7216	Intermediate Similarity	NPC329596
0.7216	Intermediate Similarity	NPC11216
0.7216	Intermediate Similarity	NPC204188
0.7209	Intermediate Similarity	NPC92801
0.7204	Intermediate Similarity	NPC474634
0.7204	Intermediate Similarity	NPC82538
0.7204	Intermediate Similarity	NPC134481
0.7204	Intermediate Similarity	NPC82623
0.7204	Intermediate Similarity	NPC237795
0.7204	Intermediate Similarity	NPC470558
0.7191	Intermediate Similarity	NPC91573
0.7191	Intermediate Similarity	NPC237460
0.7191	Intermediate Similarity	NPC73875
0.7191	Intermediate Similarity	NPC107059
0.7191	Intermediate Similarity	NPC202642
0.7191	Intermediate Similarity	NPC106364
0.7191	Intermediate Similarity	NPC470362
0.7191	Intermediate Similarity	NPC46160
0.7191	Intermediate Similarity	NPC113733
0.7191	Intermediate Similarity	NPC240604
0.7191	Intermediate Similarity	NPC321016
0.7191	Intermediate Similarity	NPC253190
0.7191	Intermediate Similarity	NPC300324
0.7191	Intermediate Similarity	NPC321381
0.7188	Intermediate Similarity	NPC474668
0.7188	Intermediate Similarity	NPC475664
0.7176	Intermediate Similarity	NPC208999
0.7176	Intermediate Similarity	NPC94192
0.7174	Intermediate Similarity	NPC47761
0.7174	Intermediate Similarity	NPC264245
0.7174	Intermediate Similarity	NPC242350
0.7174	Intermediate Similarity	NPC142163
0.7174	Intermediate Similarity	NPC70927
0.7158	Intermediate Similarity	NPC299068
0.7158	Intermediate Similarity	NPC269058
0.7158	Intermediate Similarity	NPC261266
0.7158	Intermediate Similarity	NPC71520
0.7158	Intermediate Similarity	NPC477604
0.7158	Intermediate Similarity	NPC475069
0.7158	Intermediate Similarity	NPC175145
0.7143	Intermediate Similarity	NPC209430
0.7143	Intermediate Similarity	NPC97404

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 NPC224552 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	2365
0.2-0.3	4322
0.3-0.4	1694
0.4-0.5	266
0.5-0.6	228
0.6-0.7	59
0.7-0.8	1
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
0.7333	Intermediate Similarity	NPD7645	Phase 2
0.7253	Intermediate Similarity	NPD7525	Registered
0.7079	Intermediate Similarity	NPD6942	Approved
0.7079	Intermediate Similarity	NPD7339	Approved
0.7	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6933	Approved
0.6634	Remote Similarity	NPD6079	Approved
0.6633	Remote Similarity	NPD3618	Phase 1
0.66	Remote Similarity	NPD5328	Approved
0.6598	Remote Similarity	NPD4786	Approved
0.6593	Remote Similarity	NPD4784	Approved
0.6593	Remote Similarity	NPD6926	Approved
0.6593	Remote Similarity	NPD4785	Approved
0.6593	Remote Similarity	NPD6924	Approved
0.6562	Remote Similarity	NPD3667	Approved
0.6556	Remote Similarity	NPD4243	Approved
0.6522	Remote Similarity	NPD8264	Approved
0.6471	Remote Similarity	NPD7515	Phase 2
0.6408	Remote Similarity	NPD4202	Approved
0.64	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7150	Approved
0.6374	Remote Similarity	NPD7152	Approved
0.6374	Remote Similarity	NPD7151	Approved
0.6354	Remote Similarity	NPD4748	Discontinued
0.6354	Remote Similarity	NPD7509	Discontinued
0.6333	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD7144	Approved
0.6264	Remote Similarity	NPD7143	Approved
0.6263	Remote Similarity	NPD3666	Approved
0.6263	Remote Similarity	NPD3133	Approved
0.6263	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD4195	Approved
0.6238	Remote Similarity	NPD7524	Approved
0.6226	Remote Similarity	NPD5222	Approved
0.6226	Remote Similarity	NPD5221	Approved
0.6226	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6932	Approved
0.6204	Remote Similarity	NPD5286	Approved
0.6204	Remote Similarity	NPD4696	Approved
0.6204	Remote Similarity	NPD5285	Approved
0.619	Remote Similarity	NPD7748	Approved
0.6186	Remote Similarity	NPD6930	Phase 2
0.6186	Remote Similarity	NPD6931	Approved
0.617	Remote Similarity	NPD4190	Phase 3
0.617	Remote Similarity	NPD5275	Approved
0.6168	Remote Similarity	NPD4755	Approved
0.6168	Remote Similarity	NPD5173	Approved
0.6154	Remote Similarity	NPD6923	Approved
0.6154	Remote Similarity	NPD6922	Approved
0.6147	Remote Similarity	NPD5223	Approved
0.6146	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5290	Discontinued
0.6091	Remote Similarity	NPD5226	Approved
0.6091	Remote Similarity	NPD5225	Approved
0.6091	Remote Similarity	NPD4633	Approved
0.6091	Remote Similarity	NPD7632	Discontinued
0.6091	Remote Similarity	NPD5224	Approved
0.6091	Remote Similarity	NPD5211	Phase 2
0.6082	Remote Similarity	NPD6929	Approved
0.6075	Remote Similarity	NPD4697	Phase 3
0.6055	Remote Similarity	NPD4700	Approved
0.604	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD5175	Approved
0.6036	Remote Similarity	NPD5174	Approved
0.602	Remote Similarity	NPD7514	Phase 3
0.602	Remote Similarity	NPD7332	Phase 2
0.6019	Remote Similarity	NPD7902	Approved
0.6017	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD6695	Phase 3
0.6	Remote Similarity	NPD4159	Approved
0.5982	Remote Similarity	NPD5141	Approved
0.5979	Remote Similarity	NPD3671	Phase 1
0.5979	Remote Similarity	NPD7145	Approved
0.5965	Remote Similarity	NPD6899	Approved
0.5965	Remote Similarity	NPD6881	Approved
0.5963	Remote Similarity	NPD7638	Approved
0.5962	Remote Similarity	NPD4753	Phase 2
0.5943	Remote Similarity	NPD6399	Phase 3
0.5941	Remote Similarity	NPD3668	Phase 3
0.5941	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5739	Approved
0.5929	Remote Similarity	NPD6675	Approved
0.5929	Remote Similarity	NPD7128	Approved
0.5929	Remote Similarity	NPD6402	Approved
0.5918	Remote Similarity	NPD6683	Phase 2
0.5909	Remote Similarity	NPD7639	Approved
0.5909	Remote Similarity	NPD7640	Approved
0.5909	Remote Similarity	NPD368	Approved
0.59	Remote Similarity	NPD4223	Phase 3
0.59	Remote Similarity	NPD4221	Approved
0.5897	Remote Similarity	NPD8297	Approved
0.5893	Remote Similarity	NPD4754	Approved
0.5882	Remote Similarity	NPD6893	Approved
0.5882	Remote Similarity	NPD5329	Approved
0.5877	Remote Similarity	NPD5697	Approved
0.5876	Remote Similarity	NPD5776	Phase 2
0.5876	Remote Similarity	NPD6925	Approved
0.5862	Remote Similarity	NPD6883	Approved
0.5862	Remote Similarity	NPD7290	Approved
0.5862	Remote Similarity	NPD7102	Approved
0.5847	Remote Similarity	NPD4632	Approved
0.5833	Remote Similarity	NPD5210	Approved
0.5833	Remote Similarity	NPD7115	Discovery
0.5833	Remote Similarity	NPD4629	Approved
0.5826	Remote Similarity	NPD6011	Approved
0.5826	Remote Similarity	NPD4730	Approved
0.5826	Remote Similarity	NPD4729	Approved
0.5826	Remote Similarity	NPD7320	Approved
0.5825	Remote Similarity	NPD4519	Discontinued
0.5825	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5279	Phase 3
0.5825	Remote Similarity	NPD4623	Approved
0.5818	Remote Similarity	NPD4225	Approved
0.5812	Remote Similarity	NPD6649	Approved
0.5812	Remote Similarity	NPD8130	Phase 1
0.5812	Remote Similarity	NPD6869	Approved
0.5812	Remote Similarity	NPD6650	Approved
0.5812	Remote Similarity	NPD6617	Approved
0.5812	Remote Similarity	NPD6847	Approved
0.58	Remote Similarity	NPD6898	Phase 1
0.58	Remote Similarity	NPD6902	Approved
0.5789	Remote Similarity	NPD4768	Approved
0.5789	Remote Similarity	NPD4767	Approved
0.5784	Remote Similarity	NPD4197	Approved
0.5776	Remote Similarity	NPD6012	Approved
0.5776	Remote Similarity	NPD6373	Approved
0.5776	Remote Similarity	NPD6014	Approved
0.5776	Remote Similarity	NPD6372	Approved
0.5776	Remote Similarity	NPD6013	Approved
0.5769	Remote Similarity	NPD7750	Discontinued
0.5769	Remote Similarity	NPD3573	Approved
0.5763	Remote Similarity	NPD6882	Approved
0.5745	Remote Similarity	NPD4787	Phase 1
0.5741	Remote Similarity	NPD7900	Approved
0.5741	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD5701	Approved
0.5727	Remote Similarity	NPD6083	Phase 2
0.5727	Remote Similarity	NPD6084	Phase 2
0.5726	Remote Similarity	NPD5249	Phase 3
0.5726	Remote Similarity	NPD5169	Approved
0.5726	Remote Similarity	NPD5250	Approved
0.5726	Remote Similarity	NPD5247	Approved
0.5726	Remote Similarity	NPD5251	Approved
0.5726	Remote Similarity	NPD5135	Approved
0.5726	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD5248	Approved
0.5701	Remote Similarity	NPD6411	Approved
0.57	Remote Similarity	NPD4695	Discontinued
0.569	Remote Similarity	NPD5168	Approved
0.569	Remote Similarity	NPD5128	Approved
0.569	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD4788	Approved
0.5678	Remote Similarity	NPD5215	Approved
0.5678	Remote Similarity	NPD5216	Approved
0.5678	Remote Similarity	NPD5127	Approved
0.5678	Remote Similarity	NPD5217	Approved
0.5678	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD4688	Approved
0.5673	Remote Similarity	NPD4690	Approved
0.5673	Remote Similarity	NPD4693	Phase 3
0.5673	Remote Similarity	NPD7521	Approved
0.5673	Remote Similarity	NPD6684	Approved
0.5673	Remote Similarity	NPD4689	Approved
0.5673	Remote Similarity	NPD4138	Approved
0.5673	Remote Similarity	NPD7334	Approved
0.5673	Remote Similarity	NPD6409	Approved
0.5673	Remote Similarity	NPD5330	Approved
0.5673	Remote Similarity	NPD7146	Approved
0.5673	Remote Similarity	NPD5205	Approved
0.5673	Remote Similarity	NPD5690	Phase 2
0.566	Remote Similarity	NPD6051	Approved
0.5641	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.561	Remote Similarity	NPD7516	Approved
0.5603	Remote Similarity	NPD6412	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