NPASS Compound

Structure

CID324233 OpenBabel06191716172D 32 34 0 0 1 0 0 0 0 0999 V2000 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 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 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 -1.7321 -0.0000 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 -2.5981 0.5000 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 -0.0000 2.0000 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 4.3301 3.5000 0.0000 O 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 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 2 0 0 0 0 4 13 1 0 0 0 0 5 7 1 0 0 0 0 5 12 2 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 14 2 0 0 0 0 9 20 1 0 0 0 0 10 16 1 0 0 0 0 10 19 1 0 0 0 0 11 17 2 0 0 0 0 11 32 1 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 15 22 2 0 0 0 0 15 23 1 0 0 0 0 16 22 1 0 0 0 0 16 25 2 0 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 21 25 1 0 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 24 31 2 0 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.17
Volume:	450.454
LogP:	4.496
LogD:	2.335
LogS:	-3.26
# Rotatable Bonds:	6
TPSA:	131.36
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.287
Synthetic Accessibility Score:	3.695
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.103
MDCK Permeability:	8.883538612280972e-06
Pgp-inhibitor:	0.057
Pgp-substrate:	0.951
Human Intestinal Absorption (HIA):	0.08
20% Bioavailability (F20%):	0.95
30% Bioavailability (F30%):	0.532

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	93.89105987548828%
Volume Distribution (VD):	0.553
Pgp-substrate:	4.832139492034912%

ADMET: Metabolism

CYP1A2-inhibitor:	0.375
CYP1A2-substrate:	0.171
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.721
CYP2C9-substrate:	0.404
CYP2D6-inhibitor:	0.299
CYP2D6-substrate:	0.197
CYP3A4-inhibitor:	0.081
CYP3A4-substrate:	0.072

ADMET: Excretion

Clearance (CL):	7.834
Half-life (T1/2):	0.822

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.607
Drug-inuced Liver Injury (DILI):	0.716
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.651
Maximum Recommended Daily Dose:	0.308
Skin Sensitization:	0.936
Carcinogencity:	0.138
Eye Corrosion:	0.003
Eye Irritation:	0.437
Respiratory Toxicity:	0.101

Download Data

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

Natural Product: NPC324233

Natural Product ID:	NPC324233
*Common Name:**	(+/-)-Millewanin H
IUPAC Name:	3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-(2-hydroxy-3-methylbut-3-enyl)-6-(3-methylbut-2-enyl)chromen-4-one
Synonyms:	(+/-)-Millewanin H
Standard InCHIKey:	RZHIZFURFGRHHQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H26O7/c1-12(2)5-7-15-22(29)16(10-19(27)13(3)4)25-21(23(15)30)24(31)17(11-32-25)14-6-8-18(26)20(28)9-14/h5-6,8-9,11,19,26-30H,3,7,10H2,1-2,4H3
SMILES:	CC(=CCc1c(O)c(CC(C(=C)C)O)c2c(c1O)c(=O)c(co2)c1ccc(c(c1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523654
PubChem CID:	11597321
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003526] 6-prenylated isoflavanones

*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
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16441086]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22654	Millettia pachycarpa	Species	Fabaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	IC50	=	18000.0	nM	PMID[570242]

☑ 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 NPC324233 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	423
0.1-0.2	1646
0.2-0.3	3917
0.3-0.4	9663
0.4-0.5	8724
0.5-0.6	3581
0.6-0.7	4882
0.7-0.8	5004
0.8-0.85	2463
0.85-0.9	1779
0.9-0.95	595
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC323626
0.9793	High Similarity	NPC38545
0.9793	High Similarity	NPC171916
0.9724	High Similarity	NPC238279
0.9724	High Similarity	NPC166036
0.9724	High Similarity	NPC203077
0.966	High Similarity	NPC256406
0.9597	High Similarity	NPC321779
0.953	High Similarity	NPC192083
0.953	High Similarity	NPC213896
0.9521	High Similarity	NPC51070
0.9521	High Similarity	NPC222298
0.9474	High Similarity	NPC328102
0.947	High Similarity	NPC474055
0.947	High Similarity	NPC78103
0.947	High Similarity	NPC472598
0.947	High Similarity	NPC291508
0.9467	High Similarity	NPC134287
0.9467	High Similarity	NPC130589
0.9467	High Similarity	NPC39184
0.9463	High Similarity	NPC106976
0.9459	High Similarity	NPC85131
0.9459	High Similarity	NPC88804
0.9459	High Similarity	NPC10467
0.9459	High Similarity	NPC3825
0.9456	High Similarity	NPC194653
0.9456	High Similarity	NPC203747
0.9456	High Similarity	NPC80710
0.9456	High Similarity	NPC139364
0.9456	High Similarity	NPC254702
0.9448	High Similarity	NPC242893
0.9448	High Similarity	NPC476178
0.9448	High Similarity	NPC117836
0.9448	High Similarity	NPC38065
0.9448	High Similarity	NPC51887
0.9448	High Similarity	NPC475705
0.9412	High Similarity	NPC474038
0.9412	High Similarity	NPC26326
0.9408	High Similarity	NPC53545
0.9408	High Similarity	NPC117418
0.9408	High Similarity	NPC22192
0.9404	High Similarity	NPC170026
0.9404	High Similarity	NPC291878
0.9404	High Similarity	NPC35038
0.9404	High Similarity	NPC278778
0.9404	High Similarity	NPC282307
0.9404	High Similarity	NPC195796
0.94	High Similarity	NPC124714
0.94	High Similarity	NPC93552
0.94	High Similarity	NPC298692
0.94	High Similarity	NPC74924
0.9396	High Similarity	NPC154345
0.9392	High Similarity	NPC139293
0.9392	High Similarity	NPC195763
0.9392	High Similarity	NPC333691
0.9392	High Similarity	NPC264550
0.9392	High Similarity	NPC69430
0.9392	High Similarity	NPC200060
0.9392	High Similarity	NPC40290
0.9392	High Similarity	NPC142876
0.9392	High Similarity	NPC264289
0.9379	High Similarity	NPC471417
0.9351	High Similarity	NPC474034
0.9351	High Similarity	NPC474033
0.9351	High Similarity	NPC476247
0.9346	High Similarity	NPC476283
0.9346	High Similarity	NPC287328
0.9346	High Similarity	NPC321399
0.9346	High Similarity	NPC192686
0.9346	High Similarity	NPC282009
0.9346	High Similarity	NPC118256
0.9346	High Similarity	NPC475784
0.9346	High Similarity	NPC119209
0.9342	High Similarity	NPC27337
0.9342	High Similarity	NPC471209
0.9338	High Similarity	NPC477503
0.9338	High Similarity	NPC133392
0.9338	High Similarity	NPC45849
0.9338	High Similarity	NPC234255
0.9338	High Similarity	NPC470327
0.9338	High Similarity	NPC200761
0.9333	High Similarity	NPC209487
0.9333	High Similarity	NPC131266
0.9333	High Similarity	NPC100263
0.9333	High Similarity	NPC35763
0.9333	High Similarity	NPC269451
0.9333	High Similarity	NPC471982
0.9333	High Similarity	NPC245382
0.9333	High Similarity	NPC37684
0.9333	High Similarity	NPC63187
0.9333	High Similarity	NPC291802
0.9333	High Similarity	NPC181209
0.9333	High Similarity	NPC100971
0.9333	High Similarity	NPC216769
0.9333	High Similarity	NPC157784
0.9333	High Similarity	NPC121522
0.9329	High Similarity	NPC472279
0.9324	High Similarity	NPC218490
0.9324	High Similarity	NPC119059
0.932	High Similarity	NPC316769
0.932	High Similarity	NPC12377
0.9315	High Similarity	NPC105213
0.931	High Similarity	NPC470087
0.931	High Similarity	NPC469404
0.931	High Similarity	NPC321980
0.931	High Similarity	NPC284556
0.931	High Similarity	NPC301178
0.929	High Similarity	NPC476295
0.929	High Similarity	NPC124038
0.929	High Similarity	NPC472625
0.9286	High Similarity	NPC289771
0.9286	High Similarity	NPC198829
0.9286	High Similarity	NPC472634
0.9286	High Similarity	NPC472632
0.9286	High Similarity	NPC142252
0.9286	High Similarity	NPC471499
0.9281	High Similarity	NPC210459
0.9281	High Similarity	NPC74178
0.9281	High Similarity	NPC469658
0.9281	High Similarity	NPC184755
0.9276	High Similarity	NPC472455
0.9276	High Similarity	NPC470328
0.9276	High Similarity	NPC209614
0.9276	High Similarity	NPC472626
0.9272	High Similarity	NPC250557
0.9272	High Similarity	NPC170492
0.9272	High Similarity	NPC18727
0.9267	High Similarity	NPC227485
0.9267	High Similarity	NPC59162
0.9267	High Similarity	NPC45291
0.9267	High Similarity	NPC304295
0.9267	High Similarity	NPC205046
0.9267	High Similarity	NPC19980
0.9267	High Similarity	NPC262623
0.9262	High Similarity	NPC89442
0.9262	High Similarity	NPC183959
0.9262	High Similarity	NPC1612
0.9257	High Similarity	NPC108406
0.9257	High Similarity	NPC125449
0.9257	High Similarity	NPC188074
0.9252	High Similarity	NPC157133
0.9247	High Similarity	NPC287722
0.9241	High Similarity	NPC213659
0.9241	High Similarity	NPC144118
0.9241	High Similarity	NPC326109
0.9241	High Similarity	NPC48624
0.9241	High Similarity	NPC215311
0.9241	High Similarity	NPC80962
0.9241	High Similarity	NPC172250
0.9241	High Similarity	NPC219917
0.9241	High Similarity	NPC204985
0.9241	High Similarity	NPC259166
0.9231	High Similarity	NPC471788
0.9226	High Similarity	NPC81679
0.9226	High Similarity	NPC194427
0.9226	High Similarity	NPC472635
0.9221	High Similarity	NPC36217
0.9221	High Similarity	NPC28241
0.9221	High Similarity	NPC174953
0.9221	High Similarity	NPC470326
0.9221	High Similarity	NPC476980
0.9221	High Similarity	NPC472624
0.9221	High Similarity	NPC472631
0.9221	High Similarity	NPC472630
0.9216	High Similarity	NPC223787
0.9216	High Similarity	NPC78071
0.9216	High Similarity	NPC470402
0.9216	High Similarity	NPC52530
0.9216	High Similarity	NPC473272
0.9216	High Similarity	NPC52889
0.9216	High Similarity	NPC284820
0.9211	High Similarity	NPC168247
0.9211	High Similarity	NPC226025
0.9211	High Similarity	NPC117992
0.9211	High Similarity	NPC472280
0.9211	High Similarity	NPC113906
0.9211	High Similarity	NPC152951
0.9211	High Similarity	NPC67396
0.9211	High Similarity	NPC57674
0.9211	High Similarity	NPC230149
0.9205	High Similarity	NPC60972
0.9205	High Similarity	NPC219582
0.9205	High Similarity	NPC302950
0.9205	High Similarity	NPC236637
0.9205	High Similarity	NPC237994
0.9205	High Similarity	NPC249570
0.9205	High Similarity	NPC39732
0.92	High Similarity	NPC239363
0.92	High Similarity	NPC124478
0.92	High Similarity	NPC37348
0.92	High Similarity	NPC177308
0.92	High Similarity	NPC156953
0.9195	High Similarity	NPC294852
0.9195	High Similarity	NPC321011
0.9195	High Similarity	NPC188679
0.9184	High Similarity	NPC95751
0.9184	High Similarity	NPC301751
0.9184	High Similarity	NPC245482
0.9178	High Similarity	NPC268204
0.9178	High Similarity	NPC52789

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 NPC324233 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	375
0.1-0.2	939
0.2-0.3	1735
0.3-0.4	2623
0.4-0.5	1857
0.5-0.6	1034
0.6-0.7	400
0.7-0.8	128
0.8-0.85	35
0.85-0.9	19
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.953	High Similarity	NPD2393	Clinical (unspecified phase)
0.9205	High Similarity	NPD1934	Approved
0.92	High Similarity	NPD4380	Phase 2
0.9054	High Similarity	NPD1511	Approved
0.902	High Similarity	NPD2801	Approved
0.8933	High Similarity	NPD1512	Approved
0.8897	High Similarity	NPD1510	Phase 2
0.8875	High Similarity	NPD3818	Discontinued
0.8868	High Similarity	NPD6167	Clinical (unspecified phase)
0.8868	High Similarity	NPD6168	Clinical (unspecified phase)
0.8868	High Similarity	NPD6166	Phase 2
0.8867	High Similarity	NPD4378	Clinical (unspecified phase)
0.8782	High Similarity	NPD3882	Suspended
0.8704	High Similarity	NPD7054	Approved
0.865	High Similarity	NPD7472	Approved
0.865	High Similarity	NPD7074	Phase 3
0.8621	High Similarity	NPD1240	Approved
0.8608	High Similarity	NPD7075	Discontinued
0.8608	High Similarity	NPD4381	Clinical (unspecified phase)
0.8599	High Similarity	NPD3817	Phase 2
0.8598	High Similarity	NPD6797	Phase 2
0.8591	High Similarity	NPD1549	Phase 2
0.859	High Similarity	NPD6801	Discontinued
0.8581	High Similarity	NPD2796	Approved
0.8545	High Similarity	NPD7251	Discontinued
0.8544	High Similarity	NPD4868	Clinical (unspecified phase)
0.8535	High Similarity	NPD7096	Clinical (unspecified phase)
0.8523	High Similarity	NPD1550	Clinical (unspecified phase)
0.8523	High Similarity	NPD1552	Clinical (unspecified phase)
0.8509	High Similarity	NPD6232	Discontinued
0.8503	High Similarity	NPD1607	Approved
0.85	High Similarity	NPD5494	Approved
0.8497	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD943	Approved
0.8466	Intermediate Similarity	NPD7473	Discontinued
0.8418	Intermediate Similarity	NPD7819	Suspended
0.8383	Intermediate Similarity	NPD7808	Phase 3
0.8383	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2935	Discontinued
0.8291	Intermediate Similarity	NPD7411	Suspended
0.8253	Intermediate Similarity	NPD5844	Phase 1
0.8221	Intermediate Similarity	NPD6959	Discontinued
0.8214	Intermediate Similarity	NPD6559	Discontinued
0.8194	Intermediate Similarity	NPD6799	Approved
0.8163	Intermediate Similarity	NPD3027	Phase 3
0.8155	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD5402	Approved
0.8105	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD230	Phase 1
0.8038	Intermediate Similarity	NPD5403	Approved
0.8025	Intermediate Similarity	NPD2532	Approved
0.8025	Intermediate Similarity	NPD2534	Approved
0.8025	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1247	Approved
0.8	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1613	Approved
0.7988	Intermediate Similarity	NPD919	Approved
0.7975	Intermediate Similarity	NPD7768	Phase 2
0.7964	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD5401	Approved
0.7908	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6651	Approved
0.7885	Intermediate Similarity	NPD3750	Approved
0.7853	Intermediate Similarity	NPD1465	Phase 2
0.7821	Intermediate Similarity	NPD2800	Approved
0.7812	Intermediate Similarity	NPD920	Approved
0.7784	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4628	Phase 3
0.7746	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1551	Phase 2
0.7736	Intermediate Similarity	NPD7390	Discontinued
0.7733	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6190	Approved
0.7707	Intermediate Similarity	NPD1243	Approved
0.7697	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3926	Phase 2
0.7688	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD37	Approved
0.7673	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD9494	Approved
0.7665	Intermediate Similarity	NPD6234	Discontinued
0.7635	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2313	Discontinued
0.763	Intermediate Similarity	NPD5953	Discontinued
0.7616	Intermediate Similarity	NPD7286	Phase 2
0.7607	Intermediate Similarity	NPD3226	Approved
0.7605	Intermediate Similarity	NPD3749	Approved
0.76	Intermediate Similarity	NPD2798	Approved
0.7578	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD3748	Approved
0.7564	Intermediate Similarity	NPD2799	Discontinued
0.7546	Intermediate Similarity	NPD1653	Approved
0.7545	Intermediate Similarity	NPD4965	Approved
0.7545	Intermediate Similarity	NPD4966	Approved
0.7545	Intermediate Similarity	NPD4967	Phase 2
0.7527	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4363	Phase 3
0.7514	Intermediate Similarity	NPD4360	Phase 2
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7685	Pre-registration
0.7484	Intermediate Similarity	NPD447	Suspended
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.7468	Intermediate Similarity	NPD2344	Approved
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.7457	Intermediate Similarity	NPD3751	Discontinued
0.7457	Intermediate Similarity	NPD7228	Approved
0.7452	Intermediate Similarity	NPD7033	Discontinued
0.745	Intermediate Similarity	NPD9269	Phase 2
0.7427	Intermediate Similarity	NPD5711	Approved
0.7427	Intermediate Similarity	NPD5710	Approved
0.7405	Intermediate Similarity	NPD6778	Approved
0.7405	Intermediate Similarity	NPD6777	Approved
0.7405	Intermediate Similarity	NPD6782	Approved
0.7405	Intermediate Similarity	NPD6780	Approved
0.7405	Intermediate Similarity	NPD6779	Approved
0.7405	Intermediate Similarity	NPD6781	Approved
0.7405	Intermediate Similarity	NPD6099	Approved
0.7405	Intermediate Similarity	NPD6776	Approved
0.7405	Intermediate Similarity	NPD6100	Approved
0.7403	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD8312	Approved
0.7401	Intermediate Similarity	NPD8313	Approved
0.7394	Intermediate Similarity	NPD7458	Discontinued
0.7383	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8150	Discontinued
0.7368	Intermediate Similarity	NPD8151	Discontinued
0.7354	Intermediate Similarity	NPD7584	Approved
0.7329	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3787	Discontinued
0.7303	Intermediate Similarity	NPD1203	Approved
0.7303	Intermediate Similarity	NPD1470	Approved
0.7296	Intermediate Similarity	NPD5408	Approved
0.7296	Intermediate Similarity	NPD5404	Approved
0.7296	Intermediate Similarity	NPD5406	Approved
0.7296	Intermediate Similarity	NPD5405	Approved
0.7289	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7435	Discontinued
0.7284	Intermediate Similarity	NPD2309	Approved
0.7283	Intermediate Similarity	NPD4361	Phase 2
0.7283	Intermediate Similarity	NPD5242	Approved
0.7283	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD6832	Phase 2
0.7273	Intermediate Similarity	NPD4908	Phase 1
0.7267	Intermediate Similarity	NPD2654	Approved
0.7267	Intermediate Similarity	NPD1201	Approved
0.7262	Intermediate Similarity	NPD6844	Discontinued
0.7261	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5124	Phase 1
0.7261	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1933	Approved
0.7256	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7266	Discontinued
0.723	Intermediate Similarity	NPD1548	Phase 1
0.7219	Intermediate Similarity	NPD3972	Approved
0.7202	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7698	Approved
0.7196	Intermediate Similarity	NPD7697	Approved
0.7196	Intermediate Similarity	NPD7696	Phase 3
0.7181	Intermediate Similarity	NPD9268	Approved
0.7179	Intermediate Similarity	NPD3268	Approved
0.7176	Intermediate Similarity	NPD5353	Approved
0.7162	Intermediate Similarity	NPD5536	Phase 2
0.7158	Intermediate Similarity	NPD7870	Phase 2
0.7158	Intermediate Similarity	NPD7871	Phase 2
0.7152	Intermediate Similarity	NPD1610	Phase 2
0.7143	Intermediate Similarity	NPD6823	Phase 2
0.7135	Intermediate Similarity	NPD6535	Approved
0.7135	Intermediate Similarity	NPD6534	Approved
0.7135	Intermediate Similarity	NPD7701	Phase 2
0.7126	Intermediate Similarity	NPD7229	Phase 3
0.7125	Intermediate Similarity	NPD4308	Phase 3
0.7117	Intermediate Similarity	NPD8166	Discontinued
0.7117	Intermediate Similarity	NPD7003	Approved
0.7115	Intermediate Similarity	NPD4625	Phase 3
0.7114	Intermediate Similarity	NPD9545	Approved
0.7105	Intermediate Similarity	NPD9717	Approved
0.7101	Intermediate Similarity	NPD6386	Approved
0.7101	Intermediate Similarity	NPD6385	Approved
0.7099	Intermediate Similarity	NPD2424	Discontinued
0.7097	Intermediate Similarity	NPD3018	Phase 2
0.7095	Intermediate Similarity	NPD9493	Approved
0.7091	Intermediate Similarity	NPD4357	Discontinued
0.7079	Intermediate Similarity	NPD1729	Discontinued
0.7078	Intermediate Similarity	NPD1164	Approved
0.7078	Intermediate Similarity	NPD2797	Approved
0.707	Intermediate Similarity	NPD6798	Discontinued
0.7062	Intermediate Similarity	NPD7874	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