NPASS Compound

Structure

NPC131453 OpenBabel07101719122D 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 -2.5981 2.5000 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 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 -1.7321 1.0000 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 -0.8660 1.5000 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 -1.7321 0.0000 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 2 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 20 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 16 1 0 0 0 0 14 23 1 1 0 0 0 15 18 1 1 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 20 1 6 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:	4.944
LogD:	3.955
LogS:	-5.311
# 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:	5.466
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:	-4.543
MDCK Permeability:	2.23202514462173e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.073
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.902

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.5
Plasma Protein Binding (PPB):	94.22456359863281%
Volume Distribution (VD):	1.157
Pgp-substrate:	5.722015857696533%

ADMET: Metabolism

CYP1A2-inhibitor:	0.311
CYP1A2-substrate:	0.508
CYP2C19-inhibitor:	0.159
CYP2C19-substrate:	0.846
CYP2C9-inhibitor:	0.611
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.814
CYP3A4-substrate:	0.584

ADMET: Excretion

Clearance (CL):	8.146
Half-life (T1/2):	0.091

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.752
AMES Toxicity:	0.15
Rat Oral Acute Toxicity:	0.635
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.394
Carcinogencity:	0.47
Eye Corrosion:	0.928
Eye Irritation:	0.269
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC131453

Natural Product ID:	NPC131453
*Common Name:**	Bromosphaerodiol
IUPAC Name:	(1S,4R,4aS,4bS,5S,8R,8aS,10aS)-1-bromo-8a-(bromomethyl)-4,10a-dimethyl-8-propan-2-yl-2,3,4a,4b,5,8,9,10-octahydro-1H-phenanthrene-4,5-diol
Synonyms:	Bromosphaerodiol
Standard InCHIKey:	NGARUJAPZFEXDW-KKVUZGIASA-N
Standard InCHI:	InChI=1S/C20H32Br2O2/c1-12(2)13-5-6-14(23)16-17-18(3,9-10-20(13,16)11-21)15(22)7-8-19(17,4)24/h5-6,12-17,23-24H,7-11H2,1-4H3/t13-,14-,15-,16-,17-,18+,19+,20-/m0/s1
SMILES:	BrC[C@@]12CC[C@]3([C@H]([C@@H]2[C@H](C=C[C@H]1C(C)C)O)[C@](C)(O)CC[C@@H]3Br)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL599486
PubChem CID:	46231391
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	=	24000.0	nM	PMID[511241]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	31000.0	nM	PMID[511241]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	26000.0	nM	PMID[511241]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	20000.0	nM	PMID[511241]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	22000.0	nM	PMID[511241]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15000.0	nM	PMID[511241]

☑ 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 NPC131453 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	208
0.1-0.2	1753
0.2-0.3	7690
0.3-0.4	17261
0.4-0.5	7883
0.5-0.6	5866
0.6-0.7	1729
0.7-0.8	287
0.8-0.85	10
0.85-0.9	7
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC188896
0.9213	High Similarity	NPC156912
0.8966	High Similarity	NPC239453
0.8966	High Similarity	NPC224552
0.8902	High Similarity	NPC129501
0.8901	High Similarity	NPC34732
0.8901	High Similarity	NPC92231
0.8681	High Similarity	NPC257510
0.8681	High Similarity	NPC299714
0.8256	Intermediate Similarity	NPC311891
0.8235	Intermediate Similarity	NPC476610
0.8214	Intermediate Similarity	NPC91594
0.814	Intermediate Similarity	NPC113024
0.809	Intermediate Similarity	NPC313115
0.8046	Intermediate Similarity	NPC476646
0.8	Intermediate Similarity	NPC470758
0.8	Intermediate Similarity	NPC470711
0.7952	Intermediate Similarity	NPC476609
0.7935	Intermediate Similarity	NPC329643
0.7931	Intermediate Similarity	NPC96362
0.7912	Intermediate Similarity	NPC174273
0.7907	Intermediate Similarity	NPC11908
0.7882	Intermediate Similarity	NPC470749
0.7882	Intermediate Similarity	NPC265588
0.7857	Intermediate Similarity	NPC201048
0.7857	Intermediate Similarity	NPC237510
0.7857	Intermediate Similarity	NPC475793
0.7857	Intermediate Similarity	NPC476366
0.7841	Intermediate Similarity	NPC249423
0.7831	Intermediate Similarity	NPC475077
0.7802	Intermediate Similarity	NPC299068
0.7765	Intermediate Similarity	NPC291503
0.7765	Intermediate Similarity	NPC32832
0.7765	Intermediate Similarity	NPC476605
0.7753	Intermediate Similarity	NPC218616
0.7753	Intermediate Similarity	NPC49964
0.7753	Intermediate Similarity	NPC87489
0.7753	Intermediate Similarity	NPC296701
0.7738	Intermediate Similarity	NPC182717
0.7727	Intermediate Similarity	NPC295131
0.7711	Intermediate Similarity	NPC34834
0.7701	Intermediate Similarity	NPC167891
0.7701	Intermediate Similarity	NPC83351
0.7692	Intermediate Similarity	NPC470360
0.7674	Intermediate Similarity	NPC106432
0.7674	Intermediate Similarity	NPC253190
0.7667	Intermediate Similarity	NPC82623
0.7647	Intermediate Similarity	NPC91858
0.7647	Intermediate Similarity	NPC243342
0.7647	Intermediate Similarity	NPC477138
0.764	Intermediate Similarity	NPC264245
0.7634	Intermediate Similarity	NPC133588
0.7624	Intermediate Similarity	NPC133921
0.7619	Intermediate Similarity	NPC167706
0.7619	Intermediate Similarity	NPC471272
0.7619	Intermediate Similarity	NPC23954
0.7619	Intermediate Similarity	NPC242001
0.7614	Intermediate Similarity	NPC209430
0.7614	Intermediate Similarity	NPC30986
0.7609	Intermediate Similarity	NPC261266
0.759	Intermediate Similarity	NPC476604
0.7586	Intermediate Similarity	NPC471798
0.7586	Intermediate Similarity	NPC130136
0.7582	Intermediate Similarity	NPC470077
0.7582	Intermediate Similarity	NPC205845
0.7582	Intermediate Similarity	NPC231310
0.7558	Intermediate Similarity	NPC35397
0.7558	Intermediate Similarity	NPC474946
0.7529	Intermediate Similarity	NPC471799
0.7528	Intermediate Similarity	NPC234193
0.7528	Intermediate Similarity	NPC164840
0.7528	Intermediate Similarity	NPC241290
0.7528	Intermediate Similarity	NPC209944
0.75	Intermediate Similarity	NPC318390
0.75	Intermediate Similarity	NPC215307
0.75	Intermediate Similarity	NPC274448
0.75	Intermediate Similarity	NPC145498
0.75	Intermediate Similarity	NPC300499
0.75	Intermediate Similarity	NPC476314
0.75	Intermediate Similarity	NPC274750
0.7474	Intermediate Similarity	NPC3345
0.7474	Intermediate Similarity	NPC329596
0.7474	Intermediate Similarity	NPC291484
0.7474	Intermediate Similarity	NPC11216
0.7474	Intermediate Similarity	NPC80561
0.7474	Intermediate Similarity	NPC204188
0.7473	Intermediate Similarity	NPC134481
0.7473	Intermediate Similarity	NPC470558
0.7471	Intermediate Similarity	NPC476606
0.7471	Intermediate Similarity	NPC247325
0.7471	Intermediate Similarity	NPC244488
0.7471	Intermediate Similarity	NPC476607
0.7471	Intermediate Similarity	NPC61080
0.747	Intermediate Similarity	NPC471238
0.7444	Intermediate Similarity	NPC47761
0.7442	Intermediate Similarity	NPC306727
0.7442	Intermediate Similarity	NPC471797
0.7442	Intermediate Similarity	NPC100334
0.7419	Intermediate Similarity	NPC139724
0.7419	Intermediate Similarity	NPC6391
0.7416	Intermediate Similarity	NPC84694
0.7416	Intermediate Similarity	NPC109546
0.7416	Intermediate Similarity	NPC81306
0.7416	Intermediate Similarity	NPC291379
0.7416	Intermediate Similarity	NPC476603
0.7416	Intermediate Similarity	NPC80530
0.7416	Intermediate Similarity	NPC28862
0.7416	Intermediate Similarity	NPC47982
0.7416	Intermediate Similarity	NPC143182
0.7416	Intermediate Similarity	NPC273410
0.7412	Intermediate Similarity	NPC110799
0.7412	Intermediate Similarity	NPC164022
0.7396	Intermediate Similarity	NPC41554
0.7396	Intermediate Similarity	NPC97404
0.7391	Intermediate Similarity	NPC474047
0.7391	Intermediate Similarity	NPC238485
0.7386	Intermediate Similarity	NPC34177
0.7386	Intermediate Similarity	NPC90979
0.7386	Intermediate Similarity	NPC40394
0.7386	Intermediate Similarity	NPC157996
0.7386	Intermediate Similarity	NPC472805
0.7386	Intermediate Similarity	NPC101475
0.7381	Intermediate Similarity	NPC9942
0.7381	Intermediate Similarity	NPC471560
0.7381	Intermediate Similarity	NPC210323
0.7368	Intermediate Similarity	NPC470361
0.7363	Intermediate Similarity	NPC202389
0.7363	Intermediate Similarity	NPC155521
0.7363	Intermediate Similarity	NPC101462
0.7363	Intermediate Similarity	NPC50964
0.7363	Intermediate Similarity	NPC470049
0.7363	Intermediate Similarity	NPC304285
0.7356	Intermediate Similarity	NPC66566
0.7356	Intermediate Similarity	NPC477923
0.7356	Intermediate Similarity	NPC133580
0.7349	Intermediate Similarity	NPC68703
0.7349	Intermediate Similarity	NPC69649
0.7349	Intermediate Similarity	NPC197805
0.734	Intermediate Similarity	NPC470620
0.734	Intermediate Similarity	NPC149224
0.7333	Intermediate Similarity	NPC102253
0.7333	Intermediate Similarity	NPC236237
0.7333	Intermediate Similarity	NPC287749
0.7333	Intermediate Similarity	NPC322313
0.7326	Intermediate Similarity	NPC130665
0.7326	Intermediate Similarity	NPC265485
0.7326	Intermediate Similarity	NPC220939
0.7326	Intermediate Similarity	NPC68443
0.7312	Intermediate Similarity	NPC157257
0.7312	Intermediate Similarity	NPC477578
0.7303	Intermediate Similarity	NPC6978
0.7303	Intermediate Similarity	NPC470396
0.7303	Intermediate Similarity	NPC98386
0.7303	Intermediate Similarity	NPC138621
0.7303	Intermediate Similarity	NPC158662
0.7303	Intermediate Similarity	NPC244385
0.7303	Intermediate Similarity	NPC285761
0.7303	Intermediate Similarity	NPC196753
0.7303	Intermediate Similarity	NPC474989
0.7303	Intermediate Similarity	NPC99168
0.7303	Intermediate Similarity	NPC167037
0.7303	Intermediate Similarity	NPC474216
0.7303	Intermediate Similarity	NPC230295
0.7303	Intermediate Similarity	NPC22955
0.7303	Intermediate Similarity	NPC253807
0.7294	Intermediate Similarity	NPC92801
0.7292	Intermediate Similarity	NPC77796
0.7292	Intermediate Similarity	NPC295668
0.7292	Intermediate Similarity	NPC92885
0.7292	Intermediate Similarity	NPC476226
0.7283	Intermediate Similarity	NPC475789
0.7283	Intermediate Similarity	NPC474634
0.7283	Intermediate Similarity	NPC470384
0.7283	Intermediate Similarity	NPC317458
0.7273	Intermediate Similarity	NPC122418
0.7273	Intermediate Similarity	NPC189883
0.7273	Intermediate Similarity	NPC265328
0.7273	Intermediate Similarity	NPC290598
0.7273	Intermediate Similarity	NPC274079
0.7273	Intermediate Similarity	NPC27765
0.7273	Intermediate Similarity	NPC477925
0.7273	Intermediate Similarity	NPC134330
0.7273	Intermediate Similarity	NPC129165
0.7273	Intermediate Similarity	NPC120098
0.7273	Intermediate Similarity	NPC30590
0.7263	Intermediate Similarity	NPC4574
0.7263	Intermediate Similarity	NPC212596
0.7263	Intermediate Similarity	NPC474668
0.7262	Intermediate Similarity	NPC2648
0.7262	Intermediate Similarity	NPC96484
0.7253	Intermediate Similarity	NPC209620
0.7253	Intermediate Similarity	NPC23852
0.7241	Intermediate Similarity	NPC469533
0.7241	Intermediate Similarity	NPC469593
0.7241	Intermediate Similarity	NPC469534
0.7234	Intermediate Similarity	NPC470955
0.7234	Intermediate Similarity	NPC82979
0.7229	Intermediate Similarity	NPC279434
0.7229	Intermediate Similarity	NPC476406
0.7229	Intermediate Similarity	NPC476039

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 NPC131453 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	2124
0.2-0.3	4330
0.3-0.4	1838
0.4-0.5	363
0.5-0.6	215
0.6-0.7	77
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	NPD7525	Registered
0.7222	Intermediate Similarity	NPD7645	Phase 2
0.6966	Remote Similarity	NPD6942	Approved
0.6966	Remote Similarity	NPD7339	Approved
0.6966	Remote Similarity	NPD8264	Approved
0.6889	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD368	Approved
0.6739	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD4784	Approved
0.6629	Remote Similarity	NPD4243	Approved
0.6596	Remote Similarity	NPD6931	Approved
0.6596	Remote Similarity	NPD6930	Phase 2
0.6596	Remote Similarity	NPD7514	Phase 3
0.6596	Remote Similarity	NPD7332	Phase 2
0.6596	Remote Similarity	NPD7509	Discontinued
0.6535	Remote Similarity	NPD6079	Approved
0.6531	Remote Similarity	NPD3618	Phase 1
0.6522	Remote Similarity	NPD6933	Approved
0.65	Remote Similarity	NPD5328	Approved
0.6495	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4786	Approved
0.6489	Remote Similarity	NPD6929	Approved
0.6471	Remote Similarity	NPD4202	Approved
0.6458	Remote Similarity	NPD3667	Approved
0.6449	Remote Similarity	NPD7632	Discontinued
0.6449	Remote Similarity	NPD5211	Phase 2
0.6392	Remote Similarity	NPD6695	Phase 3
0.6383	Remote Similarity	NPD7145	Approved
0.6373	Remote Similarity	NPD7515	Phase 2
0.6364	Remote Similarity	NPD4519	Discontinued
0.6364	Remote Similarity	NPD4623	Approved
0.6354	Remote Similarity	NPD6902	Approved
0.6333	Remote Similarity	NPD7144	Approved
0.6333	Remote Similarity	NPD7143	Approved
0.633	Remote Similarity	NPD5141	Approved
0.6327	Remote Similarity	NPD3665	Phase 1
0.6327	Remote Similarity	NPD3133	Approved
0.6327	Remote Similarity	NPD3666	Approved
0.6316	Remote Similarity	NPD4195	Approved
0.6277	Remote Similarity	NPD5776	Phase 2
0.6277	Remote Similarity	NPD6932	Approved
0.6277	Remote Similarity	NPD6925	Approved
0.6264	Remote Similarity	NPD7150	Approved
0.6264	Remote Similarity	NPD7151	Approved
0.6264	Remote Similarity	NPD7152	Approved
0.6263	Remote Similarity	NPD6893	Approved
0.6262	Remote Similarity	NPD7639	Approved
0.6262	Remote Similarity	NPD5285	Approved
0.6262	Remote Similarity	NPD5286	Approved
0.6262	Remote Similarity	NPD7640	Approved
0.6262	Remote Similarity	NPD4696	Approved
0.625	Remote Similarity	NPD4748	Discontinued
0.6237	Remote Similarity	NPD4190	Phase 3
0.6237	Remote Similarity	NPD5275	Approved
0.6226	Remote Similarity	NPD4755	Approved
0.6222	Remote Similarity	NPD6922	Approved
0.6222	Remote Similarity	NPD6923	Approved
0.6204	Remote Similarity	NPD5223	Approved
0.6186	Remote Similarity	NPD6898	Phase 1
0.6168	Remote Similarity	NPD7638	Approved
0.6147	Remote Similarity	NPD5225	Approved
0.6147	Remote Similarity	NPD5226	Approved
0.6147	Remote Similarity	NPD4633	Approved
0.6147	Remote Similarity	NPD5224	Approved
0.6139	Remote Similarity	NPD7750	Discontinued
0.6139	Remote Similarity	NPD7524	Approved
0.6132	Remote Similarity	NPD5222	Approved
0.6132	Remote Similarity	NPD5221	Approved
0.6132	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4700	Approved
0.6095	Remote Similarity	NPD7748	Approved
0.6091	Remote Similarity	NPD5174	Approved
0.6091	Remote Similarity	NPD5175	Approved
0.6075	Remote Similarity	NPD7902	Approved
0.6075	Remote Similarity	NPD5173	Approved
0.6068	Remote Similarity	NPD6274	Approved
0.6024	Remote Similarity	NPD342	Phase 1
0.6019	Remote Similarity	NPD5290	Discontinued
0.6019	Remote Similarity	NPD4753	Phase 2
0.6019	Remote Similarity	NPD6051	Approved
0.6018	Remote Similarity	NPD6881	Approved
0.6018	Remote Similarity	NPD6899	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.5982	Remote Similarity	NPD6675	Approved
0.5982	Remote Similarity	NPD5739	Approved
0.5982	Remote Similarity	NPD7128	Approved
0.5982	Remote Similarity	NPD6402	Approved
0.5981	Remote Similarity	NPD4697	Phase 3
0.5979	Remote Similarity	NPD6683	Phase 2
0.596	Remote Similarity	NPD4221	Approved
0.596	Remote Similarity	NPD4223	Phase 3
0.5946	Remote Similarity	NPD4754	Approved
0.5941	Remote Similarity	NPD5329	Approved
0.5941	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5697	Approved
0.5913	Remote Similarity	NPD6883	Approved
0.5913	Remote Similarity	NPD7102	Approved
0.5913	Remote Similarity	NPD7290	Approved
0.5905	Remote Similarity	NPD7087	Discontinued
0.5888	Remote Similarity	NPD4629	Approved
0.5888	Remote Similarity	NPD5210	Approved
0.5882	Remote Similarity	NPD5279	Phase 3
0.5882	Remote Similarity	NPD7115	Discovery
0.5882	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD7320	Approved
0.5877	Remote Similarity	NPD6011	Approved
0.5877	Remote Similarity	NPD4730	Approved
0.5877	Remote Similarity	NPD4729	Approved
0.5876	Remote Similarity	NPD3671	Phase 1
0.5872	Remote Similarity	NPD4225	Approved
0.587	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6650	Approved
0.5862	Remote Similarity	NPD8130	Phase 1
0.5862	Remote Similarity	NPD6617	Approved
0.5862	Remote Similarity	NPD6847	Approved
0.5862	Remote Similarity	NPD6649	Approved
0.5862	Remote Similarity	NPD6869	Approved
0.5842	Remote Similarity	NPD4197	Approved
0.5842	Remote Similarity	NPD3668	Phase 3
0.5841	Remote Similarity	NPD4767	Approved
0.5841	Remote Similarity	NPD4768	Approved
0.5826	Remote Similarity	NPD6013	Approved
0.5826	Remote Similarity	NPD6012	Approved
0.5826	Remote Similarity	NPD6373	Approved
0.5826	Remote Similarity	NPD6014	Approved
0.5826	Remote Similarity	NPD6372	Approved
0.5812	Remote Similarity	NPD6882	Approved
0.5812	Remote Similarity	NPD8297	Approved
0.5794	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7900	Approved
0.5789	Remote Similarity	NPD5701	Approved
0.578	Remote Similarity	NPD6083	Phase 2
0.578	Remote Similarity	NPD6084	Phase 2
0.5776	Remote Similarity	NPD5169	Approved
0.5776	Remote Similarity	NPD5251	Approved
0.5776	Remote Similarity	NPD4634	Approved
0.5776	Remote Similarity	NPD5249	Phase 3
0.5776	Remote Similarity	NPD5248	Approved
0.5776	Remote Similarity	NPD5247	Approved
0.5776	Remote Similarity	NPD5135	Approved
0.5776	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD5250	Approved
0.5766	Remote Similarity	NPD4159	Approved
0.5765	Remote Similarity	NPD4219	Approved
0.5758	Remote Similarity	NPD4821	Approved
0.5758	Remote Similarity	NPD4820	Approved
0.5758	Remote Similarity	NPD4819	Approved
0.5758	Remote Similarity	NPD4695	Discontinued
0.5758	Remote Similarity	NPD4822	Approved
0.5755	Remote Similarity	NPD7637	Suspended
0.5755	Remote Similarity	NPD6411	Approved
0.5743	Remote Similarity	NPD4788	Approved
0.5739	Remote Similarity	NPD5128	Approved
0.5728	Remote Similarity	NPD7334	Approved
0.5728	Remote Similarity	NPD5205	Approved
0.5728	Remote Similarity	NPD5330	Approved
0.5728	Remote Similarity	NPD4138	Approved
0.5728	Remote Similarity	NPD4689	Approved
0.5728	Remote Similarity	NPD6409	Approved
0.5728	Remote Similarity	NPD7146	Approved
0.5728	Remote Similarity	NPD6684	Approved
0.5728	Remote Similarity	NPD5690	Phase 2
0.5728	Remote Similarity	NPD4688	Approved
0.5728	Remote Similarity	NPD4693	Phase 3
0.5728	Remote Similarity	NPD4690	Approved
0.5728	Remote Similarity	NPD7521	Approved
0.5726	Remote Similarity	NPD5217	Approved
0.5726	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD5127	Approved
0.5726	Remote Similarity	NPD5215	Approved
0.5726	Remote Similarity	NPD5216	Approved
0.5714	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD5778	Approved
0.5701	Remote Similarity	NPD5779	Approved
0.5691	Remote Similarity	NPD7503	Approved
0.5684	Remote Similarity	NPD4732	Discontinued
0.5673	Remote Similarity	NPD3573	Approved
0.566	Remote Similarity	NPD7136	Phase 2
0.5638	Remote Similarity	NPD4787	Phase 1
0.5631	Remote Similarity	NPD1696	Phase 3
0.563	Remote Similarity	NPD4632	Approved
0.5625	Remote Similarity	NPD5344	Discontinued
0.5619	Remote Similarity	NPD6903	Approved
0.5619	Remote Similarity	NPD4722	Approved
0.5619	Remote Similarity	NPD4723	Approved
0.5619	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD5284	Approved
0.5607	Remote Similarity	NPD5281	Approved
0.5607	Remote Similarity	NPD8034	Phase 2
0.5607	Remote Similarity	NPD8035	Phase 2
0.5603	Remote Similarity	NPD5168	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